[ CAS No. 89-01-0 ] {[proInfo.proName]}

Name: 89-01-0|Pyrazine-2,3-dicarboxylic acid|98%
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SKU: A164253
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Quality Control of [ 89-01-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 89-01-0 ]

CAS No. :	89-01-0	MDL No. :	MFCD00006131
Formula :	C₆H₄N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZUCRGHABDDWQPY-UHFFFAOYSA-N
M.W :	168.11	Pubchem ID :	66628
Synonyms :	2,3-Dicarboxypyrazine

Calculated chemistry of [ 89-01-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	35.95
TPSA :	100.38 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.22
Log Po/w (XLOGP3) :	-0.67
Log Po/w (WLOGP) :	-0.13
Log Po/w (MLOGP) :	-1.53
Log Po/w (SILICOS-IT) :	-0.32
Consensus Log Po/w :	-0.57

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-0.7
Solubility :	33.7 mg/ml ; 0.2 mol/l
Class :	Very soluble
Log S (Ali) :	-0.96
Solubility :	18.3 mg/ml ; 0.109 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.39
Solubility :	68.0 mg/ml ; 0.405 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 89-01-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89-01-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 89-01-0 ]
Downstream synthetic route of [ 89-01-0 ]

[ 89-01-0 ] Synthesis Path-Upstream 1~15

1
[ 89-01-0 ]
[ 98-97-5 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984, vol. 23, # 9, p. 850
[2] Journal of the Chemical Society, 1937, p. 911,917
[3] Journal of the American Chemical Society, 1940, vol. 62, p. 664
[4] Patent: US2675384, 1952, ,
[5] Annali di Chimica (Rome, Italy), 1958, vol. 48, p. 239,242

2
[ 89-01-0 ]
[ 290-37-9 ]
[ 98-97-5 ]

Reference： [1] Chemische Berichte, 1907, vol. 40, p. 4852
[2] Chemische Berichte, 1907, vol. 40, p. 4852

3
[ 89-01-0 ]
[ 98-96-4 ]

Reference： [1] Journal of the American Chemical Society, 1940, vol. 62, p. 664

4
[ 89-01-0 ]
[ 57-13-6 ]
[ 98-96-4 ]

Reference： [1] Patent: US2705714, 1952, ,

5
[ 89-01-0 ]
[ 6164-79-0 ]

Reference： [1] Journal of the American Chemical Society, 1940, vol. 62, p. 664

6
[ 89-00-9 ]
[ 89-01-0 ]
[ 699-98-9 ]

Reference： [1] Patent: EP639183, 1998, B1,

7
[ 89-01-0 ]
[ 108-24-7 ]
[ 4744-50-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	for 1 h; Reflux	Pyrazine-2,3-dicarboxylic acid (4.0 g, 23.8 mmol) was dissolved in acetic anhydride (30 mL).The reaction mixture was refluxed for one hour, and subsequently cooled down to 0 °C in ice bath.The obtained crystals of pyrazine-2,3-dicarboxylic anhydride were filtered off (yield 70percent).

Reference： [1] Molecules, 2017, vol. 22, # 9,
[2] Journal of the American Chemical Society, 1953, vol. 75, p. 679
[3] Helvetica Chimica Acta, 1958, vol. 41, p. 498,509

8
[ 89-01-0 ]
[ 4744-50-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1597 - 1606
[2] Synthetic Communications, 1996, vol. 26, # 3, p. 617 - 622
[3] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 2, p. 397 - 398
[4] Chemische Berichte, 1907, vol. 40, p. 4852
[5] Chemische Berichte, 1907, vol. 40, p. 4852
[6] Patent: US2006/229357, 2006, A1, . Location in patent: Page/Page column 21
[7] Patent: US2008/146800, 2008, A1, . Location in patent: Page/Page column 4-5
[8] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 529 - 539
[9] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 158 - 168

9
[ 91-19-0 ]
[ 89-01-0 ]

Reference： [1] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
[2] Chemische Berichte, 1907, vol. 40, p. 4852
[3] Organic Syntheses, 1950, vol. 30, p. 88
[4] Journal of the American Chemical Society, 1941, vol. 63, p. 3153
[5] Journal of the American Chemical Society, 1953, vol. 75, p. 679
[6] Patent: US2710865, 1953, ,
[7] Patent: US2723974, 1953, ,
[8] Recueil des Travaux Chimiques des Pays-Bas, 1959, vol. 78, p. 109,110, 112
[9] Yakugaku Zasshi, 1957, vol. 77, p. 891,893, 894[10] Chem.Abstr., 1958, p. 1181
[11] Dalton Transactions, 2007, # 6, p. 633 - 645
[12] Patent: US2723974, 1953, ,

10
[ 921-52-8 ]
[ 131543-46-9 ]
[ 89-01-0 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984, vol. 23, # 9, p. 850

11
[ 67367-37-7 ]
[ 89-01-0 ]

Reference： [1] Polyhedron, 2012, vol. 45, # 1, p. 229 - 237,9

12
[ 66505-29-1 ]
[ 89-01-0 ]

Reference： [1] Polyhedron, 2012, vol. 45, # 1, p. 229 - 237,9

13
[ 70546-26-8 ]
[ 89-01-0 ]

Reference： [1] Polyhedron, 2012, vol. 45, # 1, p. 229 - 237,9

14
[ 13481-25-9 ]
[ 89-01-0 ]

Reference： [1] Agricultural and Biological Chemistry, 1981, vol. 45, # 9, p. 2129 - 2130
[2] Roczniki Chemii, vol. 8, p. 165[3] Chem.Abstr., 1928, vol. 22, p. 4475[4] Chem. Zentralbl., 1928, vol. 99, # II, p. 440
[5] Journal of the Chemical Society, 1937, p. 1432,1436
[6] Polyhedron, 2012, vol. 45, # 1, p. 229 - 237,9
[7] Synlett, 2017, vol. 28, # 7, p. 851 - 857

15
[ 4744-50-7 ]
[ 7732-18-5 ]
[ 89-01-0 ]

Reference： [1] Chemische Berichte, 1907, vol. 40, p. 4852

[ 89-01-0 ] Synthesis Path-Downstream 1~83

1
[ 91-19-0 ]
[ 89-01-0 ]

Reference： [1]Helvetica Chimica Acta,1994,vol. 77,p. 1549 - 1556
[2]Chemische Berichte,1907,vol. 40,p. 4852
[3]Organic Syntheses,1950,vol. 30,p. 88
[4]Journal of the American Chemical Society,1941,vol. 63,p. 3153
[5]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1957,vol. 77,p. 891,893, 894
Chem.Abstr.,1958,p. 1181
[6]Dalton Transactions,2007,p. 633 - 645
[7]Patent: US2723974,1953,

2
[ 67-56-1 ]
[ 89-01-0 ]
[ 6164-77-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	hydrogenchloride; In water; for 16h;pH 2;Heating / reflux;	2, 3-PYRAZINEDICARBOXYLICACID (21.9 g, 0.13 mol) was dissolved in MEOH (400 ML) and the pH was adjusted to 2 with HCl. This mixture was heated at reflux for 16 hrs. After evaporating MEOH, the residue was CO-EVAPORATED two times with toluene and dried in a vacuum oven to furnish 26.03 g 2, 3-PYRAZINEMETHYLDICARBOXYLATE. MS: [M + H]+ = 197
47%	With sulfuric acid; at 75℃; for 16.75h;	To a mixture of pyrazine-2,3-dicarboxylic acid (20 g, 119 mmol, 1 equiv. ) was added MeOH (80 mL) followed by dropwise addition of concentrated H2S04 (36 mL, 680 mmol, 5.7 equiv. ) over 45 minutes. This method is similar to that that cited for a different substrate (J. Am. Chem. Soc., 73, 1951, 5614 - 5616). The reaction was heated at 75 C for 16 hours and then cooled and quenched with water (200 mL). It was extracted with EtOAc (4 x 60 mL) and the organic layer washed several times with water (3 x 50 ml), saturated NaHC03 (50 ml), brine solution (50 mL). It was dried over Na2S04, filtered and concentrated in vacuo to yield pyrazine-2,3- dicarboxylic acid methyl ester 241 as a brown solid (47 %, 10.97 g, 55.9 mmol). ¹H NMR (300 MHz) CDC13 No. 8.79 (d, J= 2.7 Hz, 2 H), 4.05 (s, 3 H), 4.04 (s, 3 H). TLC Rf: 0.7 ethyl acetate/ methanol (9/1)

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1930 - 1940
[2]Patent: WO2004/96807,2004,A2 .Location in patent: Page 57; 60
[3]Dalton Transactions,2007,p. 633 - 645
[4]Agricultural and Biological Chemistry,1981,vol. 45,p. 2129 - 2130
[5]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3985 - 3988
[6]Patent: WO2005/117904,2005,A2 .Location in patent: Page/Page column 534
[7]Recueil des Travaux Chimiques des Pays-Bas,1959,vol. 78,p. 109,110, 112
[8]Chemische Berichte,1907,vol. 40,p. 4852
[9]Angewandte Chemie - International Edition,2015,vol. 54,p. 14036 - 14039

3
[ 89-01-0 ]
[ 108-24-7 ]
[ 4744-50-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	for 1h;Reflux;	Pyrazine-2,3-dicarboxylic acid (4.0 g, 23.8 mmol) was dissolved in acetic anhydride (30 mL).The reaction mixture was refluxed for one hour, and subsequently cooled down to 0 C in ice bath.The obtained crystals of pyrazine-2,3-dicarboxylic anhydride were filtered off (yield 70%).

Reference： [1]Molecules,2017,vol. 22
[2]Journal of the American Chemical Society,1953,vol. 75,p. 679

4
[ 89-01-0 ]
[ 98-97-5 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 850
[2]Journal of the Chemical Society,1937,p. 911,917
[3]Patent: US2675384,1952,
[4]Annali di Chimica,1958,vol. 48,p. 239,242

5
[ 89-01-0 ]
[ 4744-50-7 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; at 100 - 120℃;Product distribution / selectivity;	EXAMPLE 1 Preparation of 3-(5-chloropyrid -2-yl) carbamoyl-pyrazine 2 carboxylic acid In a clean, dry 500 ml R. B. flask charged acetic anhydride (162 gms) and pyrazine- 2,3, dicarboxylic acid (50 gms). The reaction mass was heated to 100-120 C. up to completion of reaction. After completion of reaction, the excess acetic anhydride was distilled under vacuum. Charged methylene dichloride (350 ml) to the above reaction mass followed by 2-amino-5- chloropyridine (40 gms) in a lot wise manner at room temperature in 30 min. The reaction mass was stirred at room temperature for 2 hrs; cooled the reaction mixture to 5-10 C. for 1 hr. The reaction mixture was filtered and washed with chilled methylene dichloride to obtain 3-(5-chloropyrid -2-yl) carbamoyl-pyrazine-2-carboxylic acid. Yield=82 gms. EXAMPLE 2; Preparation of 6-(5-chloropyrid-2-yl) 5,7-dioxo-5,6-dihydropyrrolo [3,4-b]-pyrazine; In a clean 500 ml R. B.flask charged pyrazine-2,3-dicaroxylic acid (50 gms) and acetic anhydride (162 gms). The reaction mass was heated to 110-120 C. till the completion of reaction to get pyrazine-2,3-dicarboxylic acid anhydride. After completion of the reaction, excess acetic anhydride distilled out under vacuum and furthermore charged methylene dichloride (315 ml) and 2-amino-5-chloropyridine (40 gms) in a lot wise manner at room temperature in 30 min. Further, reaction mixture was stirred for 2 hours at room temperature. The reaction mass was cooled to 5 to 10 C. for one hour, filtered the product and washed with chilled methylene dichloride. The solid was charged with methylene dichloride (235 ml), triethylamine (40.9 ml) at temp. 0-5 C. followed by ethyl chloroformate (28.1 ml). The reaction mass was stirred at 0-5 C. for 1 hr, added water (200 ml) to the reaction mixture and stirred the mass at room temperature for 1 hr to obtain the solids. The title compound thus separated was isolated by filtration.Yield=65 gms.The HPLC purity of this above product was above 99%.

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 1597 - 1606
[2]Synthetic Communications,1996,vol. 26,p. 617 - 622
[3]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 397 - 398
[4]Chemische Berichte,1907,vol. 40,p. 4852
[5]Chemische Berichte,1907,vol. 40,p. 4852
[6]Patent: US2006/229357,2006,A1 .Location in patent: Page/Page column 21
[7]Patent: US2008/146800,2008,A1 .Location in patent: Page/Page column 4-5
[8]European Journal of Medicinal Chemistry,2014,vol. 87,p. 529 - 539
[9]European Journal of Medicinal Chemistry,2016,vol. 121,p. 158 - 168

6
[ 89-01-0 ]
[ 52304-61-7 ]

Yield	Reaction Conditions	Operation in experiment
~ 100%	With thionyl chloride;N,N-dimethyl-formamide; for 5h;Reflux;	<strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (504 mg, 3.0 mmol) and DMF (2 drops) were added to 15 mL of SOCL2. The reaction mixture was refluxed for 5 hours. The SOCl2 was removed and 612 mg of pyrazine-2, 3-dicarbonyl dichloride was nearly quantitatively obtained.
~ 100%	With thionyl chloride;N,N-dimethyl-formamide; for 5h;Reflux;	<strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (504 mg, 3.0 mmol) and DMF (2 drops) were added to 15 mL of SOCl2. The reaction mixture was refluxed for 5 hours. The SOCl2 was removed and 612 mg of pyrazine-2,3-dicarbonyl dichloride was nearly quantitatively obtained.
	With thionyl chloride; for 18h;Reflux;	General procedure: o-Dicarboxylic acids (4.14 mmol) were heated under reflux in SOCl2 (50 mL) for 18 h. The solution was evaporated to dryness to give the o-diacid dichlorides, as yellow oils, which were immediately used without purification. Benzimidazole (2.12 mmol) and o-diacid dichloride (4.14 mmol) in Ac2O (50 mL) were stirred at 90 C for 15 min. The precipitated p-dione adduct was filtered, washed with Ac2O, and dried under vacuum. Compounds did not require purification, unless otherwise stated.

Reference： [1]Patent: EP2423215,2012,A1 .Location in patent: Page/Page column 9
[2]Patent: US2012/88908,2012,A1 .Location in patent: Page/Page column 5
[3]Journal of Organic Chemistry,1997,vol. 62,p. 1473 - 1480
[4]Tetrahedron Letters,2012,vol. 53,p. 3788 - 3791
[5]Chemical Biology and Drug Design,2012,vol. 80,p. 479 - 488

7
[ 89-01-0 ]
[ 51537-21-4 ]
(S)-3-tert-Butoxy-2-[3-((S)-2-tert-butoxy-1-tert-butoxycarbonyl-ethylcarbamoyl)-pyrazine-2-carbonyl]-amino}-propionic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2876 - 2882

8
[ 4744-50-7 ]
[ 7732-18-5 ]
[ 89-01-0 ]

Reference： [1]Chemische Berichte,1907,vol. 40,p. 4852

9
[ 89-01-0 ]
[ 634-95-7 ]
C₆H₄N₂O₄*C₅H₁₂N₂O*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water for 1.5h; Heating;

Reference： [1]Smith; Kennard [Australian Journal of Chemistry, 2000, vol. 53, # 11-12, p. 999 - 1001]

10
[ 89-01-0 ]
[ 84619-47-6 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2627 - 2637

11
[ 89-01-0 ]
[ 6164-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 210 °C / 3 - 4 Torr 2: HCl

Reference： [1]Hall; Spoerri [Journal of the American Chemical Society, 1940, vol. 62, p. 664]

12
[ 89-01-0 ]
[ 89601-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; hydrogen;palladium 10% on activated carbon; In water; at 50℃; for 16h;	Added to a solution of 792 mg (12 mmol) of potassium hydroxide in water (38.5 ml) were 1.00 g (6.0 mmol) of pyrazine-2,3-dicarboxylic acid and 300 mg of 10% palladium on carbon, and the mixture was stirred for 16 hours at 50 C. under hydrogen. The catalyst was removed from the reaction mixture by suction filtration through Celite. A concentrated hydrochloric acid was added until the pH of the filtrate was 3, and the solution was concentrated under reduced pressure.

Reference： [1]Patent: US6340682,2002,B1 .Location in patent: Page column 33

13
[ 89-01-0 ]
disodium pyrazine 2,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;	EXAMPLE 1 Preparation of Piperazine-2,3-Dicarboxylic Acid <strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (21.27 g, 0.127 mol) was dissolved in an aqueous solution of sodium hydroxide (10.12 g, 0.253 mol) to give disodium pyrazine-2,3-dicarboxylic acid.
	With sodium hydroxide; In water; at 20℃; for 24h;	The alkali metal salt of 2-pyrazinecarboxylic (2PCA) and 2,3-pyrazinedicarboxylic acids (2,3PDCA) was prepared by dissolving appropriate weighed amount of particular acids in hotaqueous solution of alkali metal hydroxides in a stoichiometricratio ligand/metal-1:1 for 2-pyrazinecarboxylate sand 1:2 for 2,3-pyrazinedicarboxylates. To 1 mmol of 2-PCA 10 cm3 of 0.1 mol/L alkali metal hydroxide solution in water was added. The solutions were than heated in a shaker to ca 80C for 1 h. Then, the solutions were left at RT for 24 h. Next, they were evaporated and dried at 50C for 24 h. In order to obtain alkali metal salts with 2,3-pyrazinedicarboxylic acid, 0.1 mmol of acid was diluted in 20 mL of corresponding metal hydroxide (0.1 mol L-1). Salts of 2,3-pyrazinedicarboxylate acid were prepared analogically.

Reference： [1]Patent: US2003/78237,2003,A1
[2]Journal of Thermal Analysis and Calorimetry,2016,vol. 126,p. 205 - 224

14
[ 89-01-0 ]
pyrazine-2-[N-bis-(2-hydroxyethyl)-carboxamide]-3-[N-(2-methyl-1,3-propanediol-2-yl]-carboxamide [ No CAS ]
[ 6164-77-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sulfuric acid; In methanol; ethyl acetate;	EXAMPLE 22 Pyrazine-2-[N-bis-(2-hydroxyethyl)-carboxamide]-3-[N-(2-methyl-1,3-propanediol-2-yl]-carboxamide STR37 (a) <strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> dimethylester A solution of pyrazine-2,3-dicarboxylic acid (50 g, 297.50 mmol) in 300 mL methanol and 15 mL concentrated sulfuric acid was refluxed for 24 hours. The solution was concentrated to remove MeOH, the residue redissolved in 450 mL ethylacetate and the solution extracted with 450 mL saturated NaHCO3. The organic phase was then successively extracted with 450 mL H2 O, dried over anhydrous Na2 SO4, filtered and evaporated to dryness. <strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> dimethylester was isolated as an orange oil (46.9 g, 80%). 13 C-NMR (CDCl3) delta 164.32, 145.20, 144.41, 52.90.

Reference： [1]Patent: US5972926,1999,A

15
[ 89-01-0 ]
[ 6164-77-8 ]
[ 115-69-5 ]
N,N'-Bis(1,3-dihydroxy-2-methylprop-2-yl)pyrazine-2,3-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With NMM; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; In aq CF3 COOH; ethanol; N,N-dimethyl-formamide; acetonitrile;	EXAMPLE 7 N,N'-bis-(1,3-dihydroxy-2-methylprop-2-yl)pyrazine-2,3-dicarboxamide STR22 <strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (34 mg, 0.2 mmol), PyBOP (229 mg, 0.44 mmol), HOBt (60 mg, 0.44 mmol) and NMM (0.7 mL, 0.64 mmol) were dissolved in DMF (2 mL) and allowed to react for 10 min. 2-Amino-2-methyl-1,3-propanediol (46 mg, 0.44 mmol) was then added and stirring was continued overnight. The entire reaction mixture was then fractionated on a RP-HPLC column (Vydac 218TP1022, 22250 mm, 10 mL/min, 0 to 15% MeCN in 0.1% aq CF3 COOH over 40 min). Appropriate fractions were pooled, rechromatographed and lyophilised to yield the pure title compound. Alternatively, the title compound was synthesised as follows: dimethylpyrazine-2,3-dicarboxylate (1.5 g, 7.7 mmol) and 2-amino-2-methyl-1,3-propanediol (1.6 g, 15.4 mmol) in absolute ethanol (5 mL) were heated under reflux during 4 hours. The reaction mixture was then cooled and the solvent was removed under reduced pressure. The residue was chromatographed on a flash silica gel column using CHCl3 /MeOH (4:1) as the eluant. Solvents were removed in vacuo and the pure title compound (2.2 g, 85%) was obtained after recrystallisation from isopropanol/hexane. 1 H-NMR (300 MHz, CDCl3): delta 1.06 (s, 6H, 2Me), 3.48 (d, J=6.3 Hz, 8H, 4CH2), 4.29 (t, J=6.3 Hz, 4H, 4--OH), 7.64 (s, 2H, 2NH), 8.38 (s, 2H, 2CH). 13 C-NMR (75 MHz, CDCl3): delta 164.26 (CO), 145.54 (C-2,3), 143.59 (C-5,6), 65.30 (CH2), 58.66 (Cq), 18.13 (Me).

Reference： [1]Patent: US5972926,1999,A

16
[ 12148-71-9 ]
[ 89-01-0 ]
tetraethylammonium (iridium(I)(2,3-pyrazinedicarboxylato)(1,5-cyclooctadiene)) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1990,vol. 385,p. 409 - 415

17
[ 12148-71-9 ]
[ 89-01-0 ]
[ 128652-78-8 ]

Reference： [1]Journal of Organometallic Chemistry,1990,vol. 385,p. 409 - 415

18
[ 89-01-0 ]
[ 10361-79-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
79.9%	With NaOH In sodium hydroxide; water aq. NaOH; aq. soln. of Pr-compd. and 1.5 equiv. of carboxylic acid were sealed in a teflon lined stainless steel autoclave with aq. NaOH, heating at 190 °C for 62 h; elem. anal.;

Reference： [1]Zheng, Xiang-Jun; Jin, Lin-Pei; Lu, Shao-Zhe [European Journal of Inorganic Chemistry, 2002, vol. 12, p. 3356 - 3363]

19
[ 89-01-0 ]
[ 124-22-1 ]
[ 1188923-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;	N2-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-ox o-1,2-dihydropyrimidin-4-yl)-N3-dodecylpyrazine-2,3-dicarboxamide (Compound No.37) <strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (624 mg, 4.0 mmol), 1-dodecylamine (740 mg, 4.0 mmol), benzotriazole-1-yl-oxytripyrrolidinylphosphonium hexaflurophosphate (2.6 g, 4.8 mmol) and 4-dimethylaminopyridine (488 mg, 0.4 mmol) were dissolved in N,N-dimethylformamide (10 mL) and stirred at room temperature overnight. The reaction mixture was poured into water, then extracted three times with ethyl acetate. The isolated organic phase was dried with anhydrous Na2SO4. The solvent was removed by vaporizing under reduced pressure. The residue was purified by silica column chromatography (developing agent: dichloromethane/ methanol = 30/1) to produce 3-(dodecylcarbamoyl)pyrazine-2-carboxylic acid (650 mg).
	With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;	<strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (624 mg, 4.0 mmol), 1-dodecylamine (740 mg, 4.0 mmol), benzotriazole-1-yl-oxytripyrrolidinylphosphonium hexafluorophosphate (2.6 g, 4.8 mmol) and 4-dimethylaminopyridine (488 mg, 0.4 mmol) were dissolved in N,N-dimethylformamide (10 mL) and stirred at room temperature overnight. The reaction mixture was poured into water, then extracted three times with ethyl acetate. The isolated organic phase was dried with anhydrous Na2SO4. The solvent was removed by vaporizing under reduced pressure. The residue was purified by silica column chromatography (developing agent: dichloromethane/methanol=30/1) to produce 3-(dodecylcarbamoyl)pyrazine-2-carboxylic acid (650 mg).

Reference： [1]Patent: EP2423215,2012,A1 .Location in patent: Page/Page column 14
[2]Patent: US2012/88908,2012,A1 .Location in patent: Page/Page column 8-9

20
copper(II) perchlorate hexahydrate [ No CAS ]
[ 89-01-0 ]
[ 64479-78-3 ]
Cu₂(pyrazine-2,3-dicarboxylate)2(N-(4-pyridyl)isonicotinamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With NaOH In ethanol 2,3-pyrazinedicarboxylic acid, ligand dissolved in NaOH, EtOH, slowly added to Cu(ClO4)2*6H2O, stirred for 24 h at room temp.; filtered, washed with H2O, MeOH, dried at 363 K overnight; monitored by XRD;

Reference： [1]Garcia-Ricard, Omar J.; Silva-Martinez, Juan C.; Hernandez-Maldonado, Arturo J. [Dalton Transactions, 2012, vol. 41, # 29, p. 8922 - 8930]

21
[ 67-56-1 ]
[ 693-98-1 ]
[ 89-01-0 ]
[ 6046-93-1 ]
[(copper(II))2(μ3-pyrazine-2,3-dicarboxylate)(μ-pyrazine-2,3-dicarboxylate)(2-methylimidazole)3]*CH3OH*2H2O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In water; at 50℃; for 3h;	General procedure: Ten milliliters of water solution of H2pzdc (0.50 g, 3 mmol) was treated with 10 mL NH3 (25%) under stirring at 50 C. The solution was added Cu(CH3COO)2·H2O (0.59 g, 3 mmol) and immediately precipitated. This suspension was stirred for 1 h at 50 C. Then the 2-meim ligand (0.40 g, 6 mmol) in dimethylformamide/water mixtures (1:2; 15 mL) was added dropwise to this suspension. The clear solution was stirred for 2 h at 50 C and then cooled to room temperature. The blue crystals of 2 were formed, filtered, washed with 10 mL of water and dried in air.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 19 - 35

22
[ 89-01-0 ]
[ 7646-85-7 ]
[zinc(II)(μ-pyrazine-2,3-dicarboxylate)(H2O)3] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 50 - 70℃; for 5h;	General procedure: In the complex 4, the solution of H2pzdc (0.50 g, 3 mmol) in water (25 mL) was added dropwise with stirring at 50 C to a solution of ZnCl2 (0.41 g, 3 mmol) in distilled water (15 mL). The solution abruptly became suspension and precipitated. Then the 2-meim ligand (0.40 g, 6 mmol) in water (5 mL) was added dropwise to this suspension. The suspension was stirred for 5 h at 70 C. After filtering, it was put aside for crystallization process. In a few days the crystals of complex 4 were obtained.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 19 - 35

23
[ 89-01-0 ]
[ 7664-41-7 ]
[ 7646-85-7 ]
[zinc(II)(μ-pyrazine-2,3-dicarboxylate)(NH3)2(H2O)]*H2O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 50 - 70℃; for 5h;	General procedure: In the complex 4, the solution of H2pzdc (0.50 g, 3 mmol) in water (25 mL) was added dropwise with stirring at 50 C to a solution of ZnCl2 (0.41 g, 3 mmol) in distilled water (15 mL). The solution abruptly became suspension and precipitated. Then the 2-meim ligand (0.40 g, 6 mmol) in water (5 mL) was added dropwise to this suspension. The suspension was stirred for 5 h at 70 C. After filtering, it was put aside for crystallization process. In a few days the crystals of complex 4 were obtained.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 19 - 35

24
[ 288-32-4 ]
[ 89-01-0 ]
cadmium(II) chloride monohydrate [ No CAS ]
[cadmium(II)(μ-pyrazine-2,3-dicarboxylate)(imidazole)3]*0.13H2O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 50℃; for 4h;	A solution of pyrazine-2,3-dicarboxylic acid (0.50 g, 3 mmol) in water (25 mL) was added dropwise with stirring at 50 C to a solution of CdCl2·H2O (0.54 g, 3 mmol) in distilled water (25 mL). The solution immediately became suspension and was stirred for 1 h at 50 C. Then the imidazole ligand (0.40 g, 6 mmol) in water (10 mL) was added dropwise to this suspension. The clear solution was stirred for 3 h at 50 C and then cooled to room temperature. The single crystals of 6 were filtered and washed with 10 mL of water and dried in air. Anal. Calc. for C15H14.25CdN8O4.13: C, 37.14; H, 2.96; N, 23.10. Found: C, 36.43; H, 2.77; N, 22.99%; IR (cm-1, KBr): nu(H2O), 3408 s; nu(NH), 3132 s; nu(CH), 3053 s, 2949 m, 2864 m, 2721 m; nuas(COO), 1616 vs 1562 vs; nu(C=N), 1537 m; nus(COO), 1394 vs 1359.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 19 - 35

25
[ 616-47-7 ]
[ 89-01-0 ]
cadmium(II) chloride monohydrate [ No CAS ]
[cadmium(II)(μ-pyrazine-2,3-dicarboxylate)(N-methylimidazole)3]*3H2O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 50℃; for 4h;	General procedure: A solution of pyrazine-2,3-dicarboxylic acid (0.50 g, 3 mmol) in water (25 mL) was added dropwise with stirring at 50 C to a solution of CdCl2·H2O (0.54 g, 3 mmol) in distilled water (25 mL). The solution immediately became suspension and was stirred for 1 h at 50 C. Then the imidazole ligand (0.40 g, 6 mmol) in water (10 mL) was added dropwise to this suspension. The clear solution was stirred for 3 h at 50 C and then cooled to room temperature. The single crystals of 6 were filtered and washed with 10 mL of water and dried in air.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 19 - 35

26
[ 693-98-1 ]
[ 89-01-0 ]
cadmium(II) chloride monohydrate [ No CAS ]
[cadmium(II)(μ-pyrazine-2,3-dicarboxylate)(2-methylimidazole)3] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 50℃; for 4h;	General procedure: A solution of pyrazine-2,3-dicarboxylic acid (0.50 g, 3 mmol) in water (25 mL) was added dropwise with stirring at 50 C to a solution of CdCl2·H2O (0.54 g, 3 mmol) in distilled water (25 mL). The solution immediately became suspension and was stirred for 1 h at 50 C. Then the imidazole ligand (0.40 g, 6 mmol) in water (10 mL) was added dropwise to this suspension. The clear solution was stirred for 3 h at 50 C and then cooled to room temperature. The single crystals of 6 were filtered and washed with 10 mL of water and dried in air.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 19 - 35

27
[ 79-16-3 ]
[ 693-98-1 ]
[ 89-01-0 ]
[ 6046-93-1 ]
[copper(II)(pyrazine-2,3-dicarboxylate)(2-methylimidazole)3]*DMF [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In water; at 50℃; for 3h;	Ten milliliters of water solution of H2pzdc (0.50 g, 3 mmol) was treated with 10 mL NH3 (25%) under stirring at 50 C. The solution was added Cu(CH3COO)2·H2O (0.59 g, 3 mmol) and immediately precipitated. This suspension was stirred for 1 h at 50 C. Then the 2-meim ligand (0.40 g, 6 mmol) in dimethylformamide/water mixtures (1:2; 15 mL) was added dropwise to this suspension. The clear solution was stirred for 2 h at 50 C and then cooled to room temperature. The blue crystals of 2 were formed, filtered, washed with 10 mL of water and dried in air. Anal. Calc. for C21H27CuN9O5: C, 45.94; H, 4.96; N, 22.96. Found: C, 46.01; H, 4.77; N, 23.10%; IR (cm-1, KBr): nu(NH), 3118 m; nu(CH), 3118 m, 3080 m, 2962 m, 2790 m, 2698 m; nuas(COO), 1643 vs 1593 vs; nu(C=N), 1490 m; nus(COO), 1375 s, 1348 s.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 19 - 35

28
[ 693-98-1 ]
[ 89-01-0 ]
cobalt(II) chloride hexahydrate [ No CAS ]
[cobalt(II)(μ-pyrazine-2,3-dicarboxylate)(H2O)(2-methylimidazole)2] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 50℃; for 7h;	A solution of H2pzdc (0.50 g, 3 mmol) in water (25 mL) was added dropwise with stirring at 50 C to a solution of CoCl2·6H2O (0.54 g, 3 mmol) in distilled water (25 mL). The solution abruptly became suspension and was stirred for 4 h at 50 C. Then the 2-meim ligand (0.40 g, 6 mmol) in water (10 mL) was added dropwise to this suspension. The clear solution was stirred for 3 h at 50 C and then cooled to room temperature. The single crystals of 1 were formed, filtered, washed with 10 mL of water and dried in air. Anal. Calc. for C14H16CoN6O5: C, 37.37; H, 2.35; N, 14.53. Found: C, 37.33; H, 2.52; N, 14.26%; IR (cm-1, KBr): nu(H2O), 3286 s; nu(NH), 3114 m; nu(CH), 3069 w, 2974 w, 2750 w, 2634 w; nuas(COO), 1649 vs 1595 vs; nu(C=N), 1489 m; nus(COO), 1388 s, 1348 s.

Reference： [1]Inorganica Chimica Acta,2013,vol. 399,p. 19 - 35

29
[ 5910-89-4 ]
[ 89-01-0 ]
silver nitrate [ No CAS ]
[Ag₂(Hpyzdc)₂(μ-dmpyz)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide; In water;pH 7.0;	A solution of AgNO3 (0.17g, 1mmol) in water (5cm3) was added to H2pzydc (0.17g, 1mmol), also dissolved in water (10cm3), and NaOH solution was added to adjust the pH exactly to 7. Upon addition of an aqueous solution (5cm3) of dmpyz (0.10g, 1mmol) to the stirred suspension of the white precipitate that formed, a bright clear solution was obtained. Well formed pale yellow crystals of 1, of X-ray quality, were obtained within several weeks upon slow evaporation of the solvent from the solution at room temperature in the dark. Yield for 1: 88% based on Ag. Decomp.: 116C; Anal. Calc. for [C18H14N6O8Ag2]: C, 32.85; H, 2.14; N, 12.77. Found: C, 32.78; H, 2.16; N, 12.96%.

Reference： [1]Polyhedron,2013,vol. 56,p. 116 - 122

30
[ 89-01-0 ]
chloro(1-phenylpyrazole)iridium(III) dimer [ No CAS ]
tetrakis(1-phenylpyrazolato)(2,3-pyrazinedicarboxylate) diiridium(III) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium methylate; In methanol; at 20℃; for 24h;Inert atmosphere;	Example 27: Synthesis of (tetrakis(1-phenylpyrazolato)(2,3-pyrazinedicarboxylate) diiridium(III), Abbreviation; [Ir(ppz)223PDC]2) [0350] [0351] Under argon atmosphere, into a 30 mL Schlenk flask equipped with a stirrer were placed 150 mg (0.15 mmol) of di-mu-chloro-tetrakis(1-phenylpyrazolato) diiridium(III), 25 mg (0.15 mmol) of 2,3-pyrazinedicarboxylic acid, 16 mg (0.30 mmol) of sodium methoxide and 20 ml of methanol. And then, the mixture was reacted under stirring at room temperature for 24 hours. Subsequently, the precipitate was collected by filtration, and washed with methanol, and then dried under reduced pressure, to provide 97.3 mg of tetrakis(1-phenylpyrazolato)(2,3-pyrazinedicarboxylate) diiridium(III) as a dark brown solid. (58 %) [0352] Additionally, tetrakis(1-phenylpyrazolato)(2,3-pyrazinedicarboxylate) diiridium(III) had the following properties: [0353] 1H-NMR (400MHz, CD3CN, delta (ppm)); 8.94 (d, 2H), 8.87 (d, 2H), 8.03 (s, 2H), 7.84 (d, 2H), 7.66 (d, 2H), 7.62 (d, 2H), 7.24 (d, 2H), 6.95-6.85 (m, 6H), 6.74-6.62 (m, 6H), 6.18 (dd, 2H), 6.09 (dd, 2H) FD-MS (M/Z): 1080 (M-44)

Reference： [1]Patent: EP2647642,2013,A1 .Location in patent: Paragraph 0350; 0351; 0352; 0353

31
[ 89-01-0 ]
[ 13477-34-4 ]
[ 7732-18-5 ]
silver nitrate [ No CAS ]
Ag2Ca(2,3-pyrazinedicarboxalate)2(H2O) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium hydroxide; at 100℃; for 72h;pH 7;	General procedure: A mixture of AgNO3 (0.170g,0.1mmol) and H2Pzdc (0.0167g,0.1mmol) was dissolved in 6mL water. After adjusting pH value with NaOH to about 7, the Sr(NO3)2 was added to the mixture and stirred for 5min ina 10-mLTeflon-lined stainless steel vessel autoclave at the room temperature. Themixture was sealed and heated at 100C for 3 days, and then slowly cooled down to room temperature at a rate of 2C/h. Colorless block-shaped crystals were collected by filtration, washed with distilled water and air dried. (Yield: 62%,based on Ag). Anal. Calcd for C6H4AgSrN3O8 (441.61): C,16.30%, H,0.91%, N,9.51%; Found: C,16.31%, H,0.90%, N, 9.53%. IRdata(KBrpellet): 3406 (s), 1595 (m), 1557 (s), 1485 (s), 1435 (s), 1353 (m), 1298 (s), 1265 (m), 1177 (m), 1121 (m), 1083 (m), 1038 (m), 893 (m), 809 (m), 733 (m), 672 (m), 579 (m), 439 (m).

Reference： [1]Journal of Solid State Chemistry,2014,vol. 210,p. 36 - 44

32
barium(II) nitrate [ No CAS ]
[ 89-01-0 ]
[ 7732-18-5 ]
[ 1400798-03-9 ]

Yield	Reaction Conditions	Operation in experiment
37%	In N,N-dimethyl-formamide; at 100℃; for 72h;Autoclave;	General procedure: A mixtureof Ba(NO3)2 (0.048g,0.2mmol), H2Pzdc (0.0167g,0.1mmol) and 2mL of DMFand 4mL of H2O were then added.The resulting mixture was stirred for 30 min at room temperature, and then the mixture was sealed in a 10-mL Teflon-lined stainless autoclave and heated at 100C under autogenous pressure for 3 days,then cooleddown to room temperature at the rate of5C h1 and colorless block crystals were obtained. Yield: 37% based on Ba. Anal. Calcd for C6H4BaN2O5 (321.45): C,22.40%, H,1.24%, N,8.71%; Found: C,22.42%, H,1.22%, N,8.70%. IR data (KBr pellet): 3434 (m), 1655 (s), 1497 (s), 1437 (w), 1376 (m), 1282 (m), 1249 (w), 1197 (w), 1145 (s), 1107 (m), 1060 (m), 1014 (w), 986 (m), 670 (m), 663 (s). The crystals of 1 were heated to 185C in air for 2h to produce 2. Anal. Calcd for C6H2BaN2O4 (303.44): C,23.73%, H, 0.66%, N,9.23%; Found:C,23.71%,H,0.67%,N,9.25%. IR data (KBr pellet): 3410 (m), 3134 (w), 1610(s),148 5(s), 1422 (w), 1371 (m), 1279 (m), 1265 (w), 1150 (w), 1120 (s), 1107 (m), 1089 (m), 1012 (w), 987 (m), 644 (m), 620 (s). Crystal 2 was exposed to air for several days or immersed in water for 2h, resulting in complete rehydration and formation of hydrated crystal 1?. Anal. Calcd for C6H4BaN2O5 (321.45): C,22.40%, H,1.24%, N,8.71%; Found: C,22.42%, H,1.22%, N,8.70%. IR data (KBr pellet): 3434 (m), 3134 (w), 1655 (s), 1497 (s), 1437 (w), 1376 (m), 1282 (m), 1249 (w), 1197 (w), 1145 (s), 1107 (m), 1060 (m), 1014 (w), 986 (m), 670 (m), 663 (s).

Reference： [1]Journal of Solid State Chemistry,2014,vol. 210,p. 36 - 44

33
strontium nitrate [ No CAS ]
[ 89-01-0 ]
[ 7732-18-5 ]
silver nitrate [ No CAS ]
[ 1542108-70-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydroxide; at 100℃; for 72h;pH 7;	A mixture of AgNO3 (0.170g,0.1mmol) and H2Pzdc (0.0167g,0.1mmol) was dissolved in 6mL water. After adjusting pH value with NaOH to about 7, the Sr(NO3)2 was added to the mixture and stirred for 5min ina 10-mLTeflon-lined stainless steel vessel autoclave at the room temperature. Themixture was sealed and heated at 100C for 3 days, and then slowly cooled down to room temperature at a rate of 2C/h. Colorless block-shaped crystals were collected by filtration, washed with distilled water and air dried. (Yield: 62%,based on Ag). Anal. Calcd for C6H4AgSrN3O8 (441.61): C,16.30%, H,0.91%, N,9.51%; Found: C,16.31%, H,0.90%, N, 9.53%. IRdata(KBrpellet): 3406 (s), 1595 (m), 1557 (s), 1485 (s), 1435 (s), 1353 (m), 1298 (s), 1265 (m), 1177 (m), 1121 (m), 1083 (m), 1038 (m), 893 (m), 809 (m), 733 (m), 672 (m), 579 (m), 439 (m).

Reference： [1]Journal of Solid State Chemistry,2014,vol. 210,p. 36 - 44

34
[ 89-01-0 ]
gadolinium(III) nitrate hexahydrate [ No CAS ]
[Gd₂(2,3-pyrazinedicarboxylate)₃(H₂O)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 160℃; for 96h;Autoclave;	A mixture of pyrazine-2,3-carboxylic acid (0.0841 g, 0.5 mmol), Gd(NO3)3 ·6H2O (0.2167 g, 0.5 mmol), and water (10 mL) was homogenized by stirring for 30 min, then transferred into 25 mL Teflon-lined stainless steel autoclave under autogenous pressure at 160C for 4 days. After cooling the reaction system to room temperature at a rate of 5C/h, yellow block crystals were isolated.

Reference： [1]Russian Journal of Coordination Chemistry,2015,vol. 41,p. 135 - 141
Koord. Khim.,2015,vol. 41,p. 135 - 141,7
Koordinatsionnaya Khimiya,2015,vol. 41,p. 135 - 141,7

35
[ 290-37-9 ]
copper(II) nitrate trihydrate [ No CAS ]
[ 89-01-0 ]
[Cu₂(2,3-pyrazinedicarboxylate)₂(pyrazine)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.32 g	With sodium hydroxide; In water; at 25℃; for 2h;	Copper nitrate trihydrate (1.23 g, 5.0 mmol, 1.0 eq.), pyrazine (4.05 g, 50.0 mmol, 10.0 eq.), and pure water (100 mL) were added to a recovery flask (500 mL) to be mixed. To a blue transparent solution obtained, a mixed solution of a 2,3-pyrazinedicarboxylic acid (0.84 g, 5.0 mmol, 1.0 eq.) solution (80 mL) and a 1N sodium hydroxide solution (20 mL) were added dropwise. After the mixed solution was stirred at room temperature (25 C.) for 2 hours, a blue solid obtained was filtered with a Kiriyama-rohto (registered trademark), washed with pure water and methanol in this order, and dried to obtain a blue powder (porous metal complex (1)) (yield: 1.32 g).

Reference： [1]European Journal of Inorganic Chemistry,2014,vol. 2014,p. 2747 - 2752
[2]Patent: US2015/329563,2015,A1 .Location in patent: Page/Page column 9

36
[ 492-98-8 ]
zinc(II) nitrate hexahydrate [ No CAS ]
[ 89-01-0 ]
Zn⁽²⁺⁾*C₆H₆N₄*C₆H₂N₂O₄^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium hydroxide; In water; at 150℃; for 72h;pH 5.0;Autoclave; High pressure;	A mixture of Zn(NO3)2·6H2O (0.1mmol, 30mg), H2biim (0.1mmol, 13mg), H2pzdc (0.1mmol, 20mg) and H2O (8mL) was adjusted to pH 5.0 with 0.05 mol L-1 NaOH solution. It was then sealed in a 25mL Teflon reactor and heated at 150 C for 72 h. Finally the mixture was cooled to room temperature at a cooling rate of 3 C h-1 and block colorless crystals of 1 were obtained by filtration. 1 was washed with distilled water and dried in air. Yield: 47% based on the Zn(II) salt. Anal. Calc. for C12H8N6O4Zn: C, 39.42; H, 2.21; N, 22.99. Found: C, 39.40; H, 2.20; N, 22.91%. IR (KBr, cm-1): 3088 (w), 2993 (w), 2897 (w), 2777 (s), 1608 (s), 1564 (s), 1536 (s), 1457 (s), 1442 (s), 1359 (m), 1322 (m), 1231 (m), 1204 (s), 1170 (s), 1121 (m), 1107 (m), 1064 (s), 993 (s), 946 (m), 859 (s), 833 (m), 772 (m), 740 (s), 693 (s), 665 (s).

Reference： [1]Polyhedron,2015,vol. 98,p. 40 - 46

37
[ 492-98-8 ]
[ 89-01-0 ]
bis(cadmium(II) chloride pentahydrate) [ No CAS ]
Cd⁽²⁺⁾*C₆H₆N₄*C₆H₂N₂O₄^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium hydroxide; In water; at 150℃; for 72h;pH 5.0;Autoclave; High pressure;	General procedure: A mixture of Zn(NO3)2·6H2O (0.1mmol, 30mg), H2biim (0.1mmol, 13mg), H2pzdc (0.1mmol, 20mg) and H2O (8mL) was adjusted to pH 5.0 with 0.05 mol L-1 NaOH solution. It was then sealed in a 25mL Teflon reactor and heated at 150 C for 72 h. Finally the mixture was cooled to room temperature at a cooling rate of 3C h-1 and block colorless crystals of 1 were obtained by filtration. 1 was washed with distilled water and dried in air. Yield: 47% based on the Zn(II) salt.

Reference： [1]Polyhedron,2015,vol. 98,p. 40 - 46

38
[ 89-01-0 ]
cadmium sulfate monohydrate [ No CAS ]
[ 7732-18-5 ]
[ 171565-43-8 ]
[Cd(pyrazine-2,3-dicarboxylate)(1H-imidazo[4,5-f][1,10]-phenanthroline)(H₂O)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[Cd(pda)(IP)(H2O)] (1). A mixture of CdSO4¢H2O(0.0346 g), H2pda (0.0216 g), IP (0.0118 g) CH3OH (2 mL),and deionized water (10 mL) was stirred for 30 min in air.The pH of the resulting solution was adjusted to 7 usingdilute NaOH (1 mol/L) and kept at 160C for 72 h at oven,and then cooled down to 20C. The resulting crystals formedwerefiltered off, washed with water, and dried in air.C19H12CdN6O5Anal. Calcd: C, 44.16; H, 2.34; N, 16.26.Found: C, 44.55; H, 2.17; N, 16.33. IR (KBr, cm1): 3389(s); 3012(s); 1655(vs); 1512(m); 1420(s); 1355(m); 1120(s);1051(m); 807(s); 617(s); 552(m).

Reference： [1]Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry,2016,vol. 46,p. 133 - 136

39
copper(II) perchlorate hexahydrate [ No CAS ]
[ 89-01-0 ]
[ 17252-51-6 ]
[Cu₂(pydc)2(dpp)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.71 g	With sodium hydroxide; In ethanol; water; at 25℃; for 16h;	Copper perchlorate hexahydrate (0.74 g, 2.0 mmol, 1.0 eq.), pure water (100 mL), and ethanol (100 mL) were added to a recovery flask (1000 mL) to be mixed. To a blue transparent solution obtained, a mixed solution of 2,3-pyrazinedicarboxylic acid (0.34 g, 2.0 mmol, 1.0 eq.), 1,3-di(4-pyridyl)propane (0.20 g, 1.0 mmol, 0.5 eq.), 1N sodium hydroxide solution (4 mL), pure water (96 mL), and ethanol (100 mL) was added dropwise. After the mixed solution was stirred at room temperature (25 C.) for 16 hours, a blue solid obtained was filtered with a Kiriyama-rohto (registered trademark), washed with pure water and ethanol in this order, and dried to obtain a blue powder (porous metal complex (2)) (yield: 0.71 g).

Reference： [1]Patent: US2015/329563,2015,A1 .Location in patent: Page/Page column 9

40
[ 4916-57-8 ]
copper(II) perchlorate hexahydrate [ No CAS ]
[ 89-01-0 ]
[Cu₂(pydc)2(bpa)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.54 g	With sodium hydroxide; In ethanol; water; at 25℃; for 16h;	Copper perchlorate hexahydrate (0.75 g, 2.0 mmol, 1.0 eq.), pure water (100 mL), and ethanol (100 mL) were added to a recovery flask (1000 mL) to be mixed. To a blue transparent solution obtained, a mixed solution of 2,3-pyrazinedicarboxylic acid (0.33 g, 2.0 mmol, 1.0 eq.), 1,2-di(4-pyridyl)ethane (0.18 g, 1.0 mmol, 0.5 eq.), 1N sodium hydroxide solution (4 mL), pure water (96 mL), and ethanol (100 mL) was added dropwise. After the mixed solution was stirred at room temperature (25 C.) for 16 hours, a blue solid obtained was filtered with a Kiriyama-rohto (registered trademark), washed with pure water and ethanol in this order, and dried to obtain a blue powder (porous metal complex (3)) (yield: 0.54 g).

Reference： [1]Patent: US2015/329563,2015,A1 .Location in patent: Page/Page column 10

41
copper(II) perchlorate hexahydrate [ No CAS ]
[ 89-01-0 ]
[ 7732-18-5 ]
[ 16858-01-8 ]
5C₁₈H₁₈N₄*5Cu⁽²⁺⁾*2C₆H₂N₂O₄^(2-)*6ClO₄^(1-)*6H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With lithium hydroxide; In methanol; for 0.0833333h;	To a mixture of <strong>[16858-01-8]tris(2-pyridylmethyl)amine</strong>, <strong>[16858-01-8]TPA</strong> (0.146g, 0.50mmol) and Cu(ClO4)2·6H2O (0.109g, 0.50mmol) dissolved in MeOH (20mL), 2,3-pyrazine-dicarboxylic acid (H2Pyaz2,3-dc) (0.054g, 0.25mmol) which was neutralized with LiOH (0.012g, 0.5mmol) dissolved in 5.0mL H2O was added drop by drop. The resulting solution was heated for 5min on a steam-bath, filtered through Celite and then was allowed to stand at room temperature. The resulting precipitate, which was obtained after four days was collected by filtration and recrystallized from H2O to produe aqua blue single crystals of X-ray quality. These were collected by filtration, washed with propan-2-ol, Et2O and dried in air. (overall yield: 62mg, 25% based on H2Pyaz2,3-dc) Characterization: C84H88Cl6Cu5N18O38 (2516.19g/mol) Anal. Calc.: C, 40.10, H, 3.53, N, 11.13. Found: C, 40.18; H, 3.46; N, 11.22%. Selected IR bands: ?3550 (w, br) [nu(O-H) stretching)]; 1607 (s) [nu(CO)]; 1572 (w), 1464 (m), 1435 (s), 1370 (w), 1309 (w); 1073 (vs), 1050 (s) [nu(Cl-O) (ClO4-)]. UV-Vis (CH3CN): lambdamax, nm (epsilonmaxM-1cm-1 per Cu atom): ?840 (193), 967 (265). LambdaM in (CH3CN)=602Omega-1cm2mol-1.

Reference： [1]Polyhedron,2016,vol. 111,p. 45 - 52

42
[ 89-01-0 ]
silicotungstic acid hexahydrate [ No CAS ]
[ 7758-99-8 ]
([Cu(pyrazine)1.5]4(SiW₁₂O₄₀)(water)2)n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With w; In water; at 160℃; for 96h;pH 3;Autoclave;	H4SiW12O406H2O (0.1673 mmol, 0.5 g), 2,3-pyrazinedicarboxylicacid (0.1785 mmol, 0.03 g), CuSO4(0.6221mmol, 0.1 g), were dissolved in 15 mL distilled water.Continuous stirring for 1 h at room temperature, thenadjust the pH value of the mixture solution to 3 with1.0 mol/L NaOH, continue stirring for 3 h. The suspensionwas put into a 25 mL Teflon-lined autoclave and keptunder autogenous pressure at 160 C for 4 days. After thereactor was slowly cooled to room temperature over aperiod of 10 C/h, orange-red long crystals were filteredand washed with distilled water (28 % yield based on W).

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2016,vol. 84,p. 203 - 208

43
[ 89-01-0 ]
C₁₉H₂₀F₂N₂O₂*ClH [ No CAS ]
C₄₄H₄₀F₄N₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42.7 mg	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 3h;	Example 212 To a mixture of pyrazine-2,3-dicarboxylic acid (13.1 mg, 0.078 mmol) and an HCl salt of Intermediate 32 (60 mg, 0.15 mmol) in DMF (1 mL) and DIPEA (0.068 mL, 0.39 mmol), HATU (62.6 mg, 0.16 mmol) was added and the reaction mixture was stirred at rt for 3 h. The reaction was filtered and purified by preparative HPLC to afford the title compound (42.7 mg). LC-MS retention time = 2.63 min; m/z = 825.1 [M+H]+. (Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10 mM ammonium acetate; Temperature: 50 C; Gradient: 0- 100% B over 3 minutes, then a 0.75-minute hold at 100% B; Flow: 1.0 mL/min; Detection: UV at 220 nm).

Reference： [1]Patent: WO2016/172425,2016,A1 .Location in patent: Page/Page column 296; 297

44
[ 89-01-0 ]
[ 107-15-3 ]
[ 134150-46-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	at 135℃; for 0.0666667h;Microwave irradiation;	General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 501 - 504

45
[ 89-01-0 ]
[ 109-76-2 ]
6-(3-(5,7-dioxo-5H-pyrrolo[3,4-b]pyrazin-6(7H)-yl)propyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	at 135℃; for 0.0666667h;Microwave irradiation;	General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 501 - 504

46
[ 89-01-0 ]
[ 78-90-0 ]
6-(2-(5,7-dioxo-5H-pyrrolo[3,4-b]pyrazin-6(7H)-yl)propyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	at 20℃; for 0.166667h;Microwave irradiation;	General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 501 - 504

47
[ 89-01-0 ]
[ 929-59-9 ]
6-(2-(2-(2-(5,7-dioxo-5H-pyrrolo[3,4-b]pyrazin-6(7H)-yl)ethoxy)ethoxy)ethyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	at 20℃; for 0.25h;Microwave irradiation;	General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 501 - 504

48
[ 7209-38-3 ]
[ 89-01-0 ]
6-(3-(4-(3-(5,7-dioxo-5H-pyrrolo[3,4-b]pyrazin-6(7H)-yl)propyl)piperazin-1-yl)propyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	at 20℃; for 0.25h;Microwave irradiation;	General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 501 - 504

49
[ 89-01-0 ]
[ 21587-74-6 ]
6-(3-(9-(3-(5,7-dioxo-5H-pyrrolo[3,4-b]pyrazin-6(7H)-yl)propyl)-(2,4,8,10-tetraoxaspiro[5,5]-undecane-3-yl))propyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	at 120℃; for 0.0666667h;Microwave irradiation;	General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 501 - 504

50
[ 89-01-0 ]
lithium 2,3-pyrazinedicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; In water; at 20℃; for 24h;	The alkali metal salt of 2-pyrazinecarboxylic (2PCA) and 2,3-pyrazinedicarboxylic acids (2,3PDCA) was prepared by dissolving appropriate weighed amount of particular acids in hotaqueous solution of alkali metal hydroxides in a stoichiometricratio ligand/metal-1:1 for 2-pyrazinecarboxylate sand 1:2 for 2,3-pyrazinedicarboxylates. To 1 mmol of 2-PCA 10 cm3 of 0.1 mol/L alkali metal hydroxide solution in water was added. The solutions were than heated in a shaker to ca 80C for 1 h. Then, the solutions were left at RT for 24 h. Next, they were evaporated and dried at 50C for 24 h. In order to obtain alkali metal salts with 2,3-pyrazinedicarboxylic acid, 0.1 mmol of acid was diluted in 20 mL of corresponding metal hydroxide (0.1 mol L-1). Salts of 2,3-pyrazinedicarboxylate acid were prepared analogically.

Reference： [1]Journal of Thermal Analysis and Calorimetry,2016,vol. 126,p. 205 - 224

51
[ 89-01-0 ]
potassium 2,3-pyrazinedicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; at 20℃; for 24h;	The alkali metal salt of 2-pyrazinecarboxylic (2PCA) and 2,3-pyrazinedicarboxylic acids (2,3PDCA) was prepared by dissolving appropriate weighed amount of particular acids in hotaqueous solution of alkali metal hydroxides in a stoichiometricratio ligand/metal-1:1 for 2-pyrazinecarboxylate sand 1:2 for 2,3-pyrazinedicarboxylates. To 1 mmol of 2-PCA 10 cm3 of 0.1 mol/L alkali metal hydroxide solution in water was added. The solutions were than heated in a shaker to ca 80C for 1 h. Then, the solutions were left at RT for 24 h. Next, they were evaporated and dried at 50C for 24 h. In order to obtain alkali metal salts with 2,3-pyrazinedicarboxylic acid, 0.1 mmol of acid was diluted in 20 mL of corresponding metal hydroxide (0.1 mol L-1). Salts of 2,3-pyrazinedicarboxylate acid were prepared analogically.

Reference： [1]Journal of Thermal Analysis and Calorimetry,2016,vol. 126,p. 205 - 224

52
[ 89-01-0 ]
rubidium 2,3-pyrazinedicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With rubidium hydroxide; In water; at 20℃; for 24h;	The alkali metal salt of 2-pyrazinecarboxylic (2PCA) and 2,3-pyrazinedicarboxylic acids (2,3PDCA) was prepared by dissolving appropriate weighed amount of particular acids in hotaqueous solution of alkali metal hydroxides in a stoichiometricratio ligand/metal-1:1 for 2-pyrazinecarboxylate sand 1:2 for 2,3-pyrazinedicarboxylates. To 1 mmol of 2-PCA 10 cm3 of 0.1 mol/L alkali metal hydroxide solution in water was added. The solutions were than heated in a shaker to ca 80C for 1 h. Then, the solutions were left at RT for 24 h. Next, they were evaporated and dried at 50C for 24 h. In order to obtain alkali metal salts with 2,3-pyrazinedicarboxylic acid, 0.1 mmol of acid was diluted in 20 mL of corresponding metal hydroxide (0.1 mol L-1). Salts of 2,3-pyrazinedicarboxylate acid were prepared analogically.

Reference： [1]Journal of Thermal Analysis and Calorimetry,2016,vol. 126,p. 205 - 224

53
[ 89-01-0 ]
cesium 2,3-pyrazinedicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With cesium hydroxide; In water; at 20℃; for 24h;	The alkali metal salt of 2-pyrazinecarboxylic (2PCA) and 2,3-pyrazinedicarboxylic acids (2,3PDCA) was prepared by dissolving appropriate weighed amount of particular acids in hotaqueous solution of alkali metal hydroxides in a stoichiometricratio ligand/metal-1:1 for 2-pyrazinecarboxylate sand 1:2 for 2,3-pyrazinedicarboxylates. To 1 mmol of 2-PCA 10 cm3 of 0.1 mol/L alkali metal hydroxide solution in water was added. The solutions were than heated in a shaker to ca 80C for 1 h. Then, the solutions were left at RT for 24 h. Next, they were evaporated and dried at 50C for 24 h. In order to obtain alkali metal salts with 2,3-pyrazinedicarboxylic acid, 0.1 mmol of acid was diluted in 20 mL of corresponding metal hydroxide (0.1 mol L-1). Salts of 2,3-pyrazinedicarboxylate acid were prepared analogically.

Reference： [1]Journal of Thermal Analysis and Calorimetry,2016,vol. 126,p. 205 - 224

54
[ 366-18-7 ]
[ 89-01-0 ]
[ 6156-78-1 ]
[Mn(2,3-pyrazinedicarboxylic acid)(2,2'-bipyridyl)(H₂O)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		An aqueous solution (5 ml) of Mn (CH3C00) 2.4H20 (0.l mmol, 0.0245 g) and 2,2 '-bpy (0.3 mmol,0. 0468 g) in methanol (5 ml) was stirred at room temperature for 0.5 hour. Then, H2pzdc (0.10 mmol, 0.0164 g)Aqueous solution (5 mL). Continue to stir at room temperature for 2 hours, filtration, the filtrate standing, slow evaporation, about a week can be light yellowColor needle crystal. The yield was calculated to be 42% based on the metal Mun element content.

Reference： [1]Patent: CN105399773,2016,A .Location in patent: Paragraph 0016; 0017

55
[ 89-01-0 ]
1,4-bis (1H-1,2,4-triazole)butane [ No CAS ]
[ 6156-78-1 ]
[Mn(btb)0.5(pzdc) (H₂₀)2]*H₂₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		Mn (CH3C00) 2.4H20 (0.l mmol, 0.0245 g)(0.05 ml) and btb (0.3 mmol, 0.0576 g) in water (5 ml each), and the mixture was stirred at room temperature for 1 hour, and then an aqueous solution (5 ml) of H2pzdc (0.05 mmol, 0.008 g) was added. After stirring at room temperature for two hours, the filtrate was allowed to stand and slowly evaporated. After about one week, yellow needle-shaped crystals were obtained. The yield was calculated to be 40% on the basis of the content of metal eta element.

Reference： [1]Patent: CN105399774,2016,A .Location in patent: Paragraph 0016; 0017

56
[ CAS Unavailable ]
[ 89-01-0 ]
[ 116476-98-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: zinc(II) nitrate hexahydrate; 1,2-bis(1,2,4-triazol-1-yl)ethane In water at 20℃; for 2h; Stage #2: 2,3-dicarboxypyrazine In water at 20℃; for 2h;	1 Synthesis of complexes 0.1mmol of Zn (N03) 2 · 6H20 (0.098 g) and 0.1mmol of bistriazole ethane (0.0164 g) were each dissolved in 5 ml of water, and the above two solutions were mixed and stirred at room temperature for 2 hours , An aqueous solution (5 ml) of H2pzdc (0. lmmol, 0.0168 g) was added. After stirring at room temperature for two hours, the filtrate was allowed to stand and slowly evaporated. After about two weeks, white lumps of crystals were obtained. The calculated yield was 42% based on the elemental content of the metal.

Reference： [1]Current Patent Assignee: TIANJIN POLYTECHNIC UNIVERSITY - CN105399759, 2016, A Location in patent: Paragraph 0011-0012

57
[ 89-01-0 ]
[ 7732-18-5 ]
[ 5970-45-6 ]
[ 1135-32-6 ]
[Zn(μ₃-pzdc)(μ-1,2-bis(4-pyridyl)ethylene)_0.5]*3H₂O}_n [ No CAS ]
[Zn(μ₃-pzdc)(μ-1,2-bis(4-pyridyl)ethylene)_0.5]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.10%; 11%	With potassium hydroxide; at 140℃; for 144h;High pressure;	A mixture of pyrazine-2,3-dicarboxylic acid (0.198 g, 1.18 mmol),dpeten (0.215 g, 1.18 mmol), Zn(CH3COO)22H2O (0.259 g,1.18 mmol), KOH (0.066 g, 1.18 mmol), and H2O (15 mL) was placedin a Teflon-lined stainless steel vessel, heated to 140 C for 6 days,followed by cooling to room temperature at a rate of 5 Kh-1 andcolorless crystals of 1 and pale yellow solution was obtained. Theresulting solution was allowed for slowly evaporation about oneweeks and yellow block-shaped crystals were grown of 2. (For 1, 63.10% yield based on Zn(CH3COO)22H2O; Anal. Calc.C12H13N3O7Zn (1): C, 38.27; H, 3.48; N, 11.16. Found: C, 38.21; H,3.49; N, 11.15%). IR (cm1, KBr pellet): 3400 (s), 3097 (s), 2464 (w),2133 (w), 1951 (w),1658 (vs),1614 (vs), 1579 (vs),1510 (s),1467 (vs),1438 (s), 1398 (vs), 1359 (vs), 1126 (vs), 839 (s), 549 (s). For 2, 11%yield based on Zn(CH3COO)22H2O Anal. Calc. for C12H7N4O3Zn (2):C, 44.95; H, 2.20; N, 17.47. Found: C, 44.98; H, 2.22; N, 17.51%. IR(cm1, KBr pellet): 3427 (w), 3066 (w), 2680 (w), 2464 (w),1672 (s),1620 (vs), 1573 (s), 1510 (w), 1473 (m), 1429 (w), 1392 (s), 1342 (s),1120 (m), 835 (m), 549 (m).

Reference： [1]Journal of Molecular Structure,2017,vol. 1137,p. 562 - 568

58
[ 39565-07-6 ]
[ 89-01-0 ]
(5,7-dimethyl-1,8-naphthyridine-2-amine):(2,3-pyrazinedicarboxylic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.92%	In ethanol; for 0.333333h;	To a 17 methanol solution (5mL) of 12 5,7-dimethyl-1,8-naphthyridine-2-amine (34.8mg, 0.2mmol) was added 43 2,3-pyrazinedicarboxylic acid (16.8mg, 0.1mmol) in 14mL 11 ethanol. The solution was stirred for 20min, then the solution was filtered into a test tube. Colorless block crystals were isolated after 18 days from the solution at room temperature in air. The crystals were collected and dried in air to give 44 [(HL)+ · (Hpyda-) · H2O] (9), the yield was 56mg (77.92% based on L). m. p. 182-184C. Anal. Calcd for C16H17N5O5 (359.35): C, 53.43; H, 4.73; N, 19.48. Found: C, 53.32; H, 4.60; N, 19.35. Infrared spectrum (KBr disc, cm-1): 3674w (nu(HO), 3456m (nuas (NH)), 3356w (nus (NH)), 3238m, 3046m, 2982m, 2948w, 2836w, 1682s (nu(C=O)), 1602s (nuas (COO-)), 1558m, 1516m, 1472m, 1430m, 1388s (nus (COO-)), 1346m, 1304s (nu(C-O)), 1262m, 1218m, 1174m, 1134m, 1092m, 1046m, 1004m, 960m, 916m, 872m, 828m, 785m, 745m, 702m, 660m, 618m.

Reference： [1]Journal of Molecular Structure,2017,vol. 1150,p. 595 - 613

59
[ 89-01-0 ]
[ 934405-30-8 ]
3-(2-(2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamido)-5-chloro-3-methylphenylcarbonyl)hydrazinecarbonyl)pyrazine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; O?(1H?benzotriazol?1?yl)?N,N,N?,N??tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20℃; for 3h;Green chemistry;	The intermediate N- (4-chloro-2- (formylhydrazino) -6-methylphenyl) -3-bromo- 1 - (3-chloropyridin-2-yl) Pyrazole-5-carboxamide (1.00 g, 2.07 mmol) and<strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong>(0.35 g, 2.07 mmol) was dissolved in N, N-dimethylformamide (DMF) followed by coupling reagentO-benzotriazole-N, N, N ', N'-tetramethyluronium tetrafluoroborate (TBTU) (0.66 g, 2.07 mmol) was added dropwise and N, N-diisopropylethylamine (DIPEA) (0.80 g, 6.20 mmol) was added dropwise and stirred at ambient temperature for 3 h.TLC point plate tracking, the point of disappearance of raw materials, the reaction solution into 500mL saturated salt water, stirred 0.5h, fully precipitated, filtered to give the crude product, dried and purified by column chromatography.

Reference： [1]Patent: CN107011335,2017,A .Location in patent: Paragraph 0071; 0072

60
[ 89-01-0 ]
[ 1233882-37-5 ]
3-(2-(2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamido)-5-bromo-3-methylphenylcarbonyl)hydrazinecarbonyl)pyrazine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; O?(1H?benzotriazol?1?yl)?N,N,N?,N??tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20℃; for 3h;Green chemistry;	The intermediate N- (4-bromo-2- (formylhydrazino) -6-methylphenyl) -3- bromo-l- (3- chloropyridin- 2-yl) -lH- Pyrazole-5-carboxamide (1.00 g, 1.89 mmol) and<strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong>(0.32 g, 1.89 mmol) was dissolved in N, N-dimethylformamide (DMF) followed by coupling reagentO-benzotriazole-N, N, N ', N'-tetramethyluronium tetrafluoroborate (TBTU)(0.60 g, 1.89 mmol). N, N-diisopropylethylamine (DIPEA) (0.73 g, 5.68 mmol) was added dropwise and the mixture was stirred at ambient temperature for 3 h.TLC point plate tracking, the point of disappearance of raw materials, the reaction solution into 500mL saturated salt water, stirred 0.5h, fully precipitated, filtered to give the crude product, dried and purified by column chromatography.

Reference： [1]Patent: CN107011335,2017,A .Location in patent: Paragraph 0091; 0092

61
[ 89-01-0 ]
[ 106-24-1 ]
pyrazine-2,3-dicarboxylic acid digeraniol ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Perfume monomer pyrazine - 2, 3 - dicarboxylic acid II crane alcohol ester preparation method:Taking 10mmol geraniol and 5mmol pyrazine - 2, 3 - dicarboxylic acid dissolved in 100 ml dry dichloromethane in, stirring 10min after, adding 4 - dimethylamino pyridine (DMAP) (5mmol) and 1 - ethyl - (3 - dimethyl amino propyl) carbonylamino-carbodiimide hydrochloride (EDCHCl) (11mmol), stirring at the room temperature, TLC monitoring the reaction, tracking end point of the reaction. Adding water to the organic phase 50 ml wash, liquid, then 50 ml saturated sodium chloride solution, liquid, organic phase with anhydrous Na2SO4Drying, concentrated to obtain the crude product. The crude product for 50 ml dichloromethane dissolved, add 100 - 200 purpose silica gel 4g, decompression turns on lathe the dry mix type, for 80g 100 - 200 silica gel in the purpose of analyzes petroleum ether: ethyl acetate=60:1 slowly elute, concentrated, dried to obtain the target product.

Reference： [1]Patent: CN106496148,2017,A .Location in patent: Paragraph 0024-0029; 0038

62
[ 89-01-0 ]
[ 472-80-0 ]
pyrazine-2,3-dicarboxylic acid di-β-ionol ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Perfume monomer pyrazine - 2, 3 - dicarboxylic acid II - beta - violet alcohol ester preparation method:In the three flasks, adding weighed 20mmol beta - violet alcohol and 10mmol pyrazine - 2, 3 - dicarboxylic acid is dissolved in 200 ml dry dichloromethane in, stirring 10min after, adding 4 - dimethylamino pyridine (DMAP) (8mmol) and 1 - ethyl - (3 - dimethyl amino propyl) carbonylamino-carbodiimide hydrochloride (EDC·HCl) (22mmol), stirring at room temperature, TLC monitoring the reaction, the tracking reaction to the end. The organic phase is added to the purified water 100 ml washing, liquid, then 100 ml saturated sodium chloride solution, liquid, organic phase with anhydrous Na2SO4 drying, the concentrated crude product. The crude product is used for 10 ml dichloromethane dissolved, add 100 - 200 silica gel to 7g, decompression turns on lathe the dry mix type, for 100g 100 - 200 for the purpose of separation of silica gel chromatography, eluent petroleum ether: ethyl acetate=80:1 slowly elute, concentrated, dried to obtain the target product

Reference： [1]Patent: CN106496148,2017,A .Location in patent: Paragraph 0030-0035; 0039

63
[ 89-01-0 ]
aqueous cadmium chloride [ No CAS ]
[ 39677-03-7 ]
Cd₂(2,3-pzdc)(1,1′-(1,4-butanediyl)bis(benzimidazole)) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With hydrogenchloride; sodium hydroxide; In water; at 150℃; for 72h;pH 5;High pressure;	A mixture of CdCl2·2.5H2O (0.03 g, 0.13 mmol), 2,3-H2pzdc (0.02 g, 0.12 mmol), bbbi (0.03 g,0.10 mmol) and H2O (10 mL) was stirred. The pH of the mixture was adjusted to 5 with NaOH/HCl solution (0.05 mol/L) and heated at 150 C for 3 days under autogenous pressure, then cooled at a rate of 3 C/h to room temperature. Light yellow blocky crystals of 1 were separated,washed with distilled water, and dried at ambient temperature. Yield: 61% based onCd. Elemental analysis for 1: C24H20N6O4Cd (568.87). Calcd %: C, 50.63; H, 3.52; N, 14.77. Found:C, 50.82; H, 3.34; N, 14.59. IR (KBr, cm-1): 3420 (br), 3092 (w), 3022 (w), 2943 (w), 1639 (s), 1516(s), 1464 (m), 1429 (w), 1388 (m), 1345 (s), 1295 (m), 1260 (m), 1204 (m), 1167 (m), 1151 (m),1103 (m), 1011 (m), 926 (m), 769 (s), 641 (w), 606 (w).

Reference： [1]Journal of Coordination Chemistry,2017,vol. 70,p. 3971 - 3981

64
copper(II) perchlorate hexahydrate [ No CAS ]
[ 89-01-0 ]
[ 69506-92-9 ]
Cu₂(pyrazine-2,3-dicarboxylate)2(1,3-bis(imidazol-1-yl)methylbenzene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water at 20℃; for 24h;

Reference： [1]Arrieta-Pérez, Rodinson R.; Primera-Pedrozo, José N.; Exley, Jason; Hernández-Maldonado, Arturo J. [Crystal Growth and Design, 2018, vol. 18, # 3, p. 1676 - 1685]

65
[ 1072-63-5 ]
basic zinc carbonate [ No CAS ]
[ 89-01-0 ]
[ 7732-18-5 ]
3Zn⁽²⁺⁾*3C₆H₂N₂O₄^(2-)*7C₅H₆N₂*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		H2pzdc (0.336 g, 2 mmol) was dissolved in 200 ml of hot distilledwater. Then, 1 mmol (0.225 g) of ZnCO3·Zn(OH)2was added to the hot solution while stirring. The mixturewas then stirred for 4 h keeping the temperature at80C. Following this, the stirring was continued for oneday at room temperature. Finally, the excess vim (e.g. 10mmol, 0.905 mL) in 20 mL of ethanol was added to themixture and it was stirred for another day. The clear solutionobtained was allowed to crystallize and the quite lightbrown crystals were obtained with a yield of 80% (741mg). Anal. Calc. for [Zn3(pzdc)3(vim)6] · vim · 2H2O}n(C53H52N20O14Zn3, MW: 1389 g/mol): C, 45.82; H, 3.77;N, 20.16%. Found: C, 45.74; H, 3.79; N, 19.90%. SelectedIR peaks (KBr disk/cm-1): upsilon = 3432 (m,br) upsilon (O-H); 3147-3001 (m,mt) upsilon (C-H); 1651(vs,sh) upsilon (C=O); 1567 (m,sh)upsilon (C=N); 1453(m,sh) upsilon (C=C) cm-1.

Reference： [1]Journal of Chemical Sciences,2018,vol. 130

66
[ 89-01-0 ]
yttrium(lll) nitrate hexahydrate [ No CAS ]
K4[α-SiW12O40]*17H2O [ No CAS ]
O₄₀SiW₁₂^(4-)*10H₂O*2H⁽¹⁺⁾*2C₆H₂N₂O₄^(2-)*2Y⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 50%	In ethanol; water; at 80℃; for 1h;	General procedure: A 20 mL aqueous solution containing 1.70 g K4[a-SiW12O40]¢17H2O was added to a 20 mL mixed CH3CH2OH/H2O(1:1, volume ratio) solution containing 0.10 g (0.60 mmol) H2pddcand PrCl3¢7H2O (0.50 g, 1.34 mmol). The resulting mixture washeated in water bath (80C) for 1 hour and filtered after cooling.Slow evaporation at room temperature led to green crystals suitablefor X-ray diffraction within 1-2 weeks, which were collected by filtrationand dried in air (Yield: ca. 50% based on K4[a-SiW12O40]¢17H2O).

Reference： [1]Inorganic and Nano-Metal Chemistry,2018,vol. 48,p. 85 - 90

67
[ 1072-63-5 ]
[ 89-01-0 ]
cobalt(II) carbonate hydrate [ No CAS ]
C₆H₂N₂O₄^(2-)*3C₅H₆N₂*H₂O*Co⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		<strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (0.336 g, 2 mmol) was dissolvedin hot distilled water (200 mL). While the solutionwas hot, CoCO3·xH2O (0.274 g, 2 mmol) was added withstirring. The mixture was firstly stirred at 80 C for 4 h,then at room temperature for 1 day. After this, the excessof 1-vinylimidazole (i.e., 0.905 mL, 10 mmol) in ethanol(20 mL) was dropwise added to the mixture. After stirringfor one more day at room temperature, the clear solutionobtained was left to crystallize. The red-brown crystalsformed were collected. Yield: 80% (840 mg). Anal.Calc. (%) for [Co(pzdc)(vim)3]·H2O}n (C21H22CoN8O5,MW: 524.9 g mol-1): C, 48.01; H, 4.19; N, 21.34. FoundC, 47.99; H, 4.43; N, 20.98. Selected IR peaks (KBr disk/cm-1): upsilon = 3460 (m,br) upsilon(O-H); 3115-3004 (m, mt) upsilon(C-H);1651 (vs,sh) upsilon(C=O); 1562 (m, sh) upsilon(C=N); 1445 (m, sh)upsilon(C=C).

Reference： [1]Journal of the Iranian Chemical Society,2018,vol. 15,p. 1699 - 1708

68
[ 1072-63-5 ]
[ 89-01-0 ]
nickel hydroxocarbonate hydrate [ No CAS ]
C₆H₂N₂O₄^(2-)*2C₅H₆N₂*Ni⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: <strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (0.336 g, 2 mmol) was dissolvedin hot distilled water (200 mL). While the solutionwas hot, CoCO3·xH2O (0.274 g, 2 mmol) was added withstirring. The mixture was firstly stirred at 80 C for 4 h,then at room temperature for 1 day. After this, the excessof 1-vinylimidazole (i.e., 0.905 mL, 10 mmol) in ethanol(20 mL) was dropwise added to the mixture. After stirringfor one more day at room temperature, the clear solutionobtained was left to crystallize. The red-brown crystalsformed were collected. Yield: 80% (840 mg).

Reference： [1]Journal of the Iranian Chemical Society,2018,vol. 15,p. 1699 - 1708

69
[ 89-01-0 ]
[ 7732-18-5 ]
[ 5970-45-6 ]
[ 7803-57-8 ]
[Zn2(4,5-diamino-1,2-dihydropyridazine-3,6-diolato)2]·H2O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With oxalic acid; at 170℃; for 96h;pH 5-7;High pressure;	Under the room temperature, pca (0.1 mmol, 15.3 mg) andN2H4·H2O (50 muL) were added in 10 mL distilled water. After stirringfor half an hour, Zn(CH3COO)2·2H2O (0.1 mmol, 21.9 mg) was pouredinto the mixed solution. And the agitation continued about four hours.Then the mixture (pH = 5-7 adjusted by H2(C2O4)) was transferredinto a Teflon-lined stainless steel vessel (15 mL) and heated at 170 Cfor 4 days. The vessel was naturally cooled to the room temperature after 24 h. The light-yellow block crystals of 1 were obtained. Washedwith distilled water, the crystals of 1 were collected in 49% yield based on Zn. Anal. Calcd. for C8H10N8O5Zn2 1: C, 22.40, H, 2.35; N, 26.12%;Found: C, 22.16; H, 2.11; N, 26.99%. IR spectrum (cm-1): 3427 m,3324 s, 3189 s, 1645 s, 1495 s, 1447 s, 1416 s, 1338 m, 1236 s, 1181 s,1079 w, 976 w, 880 w, 805 w, 716 m, 541 w.

Reference： [1]Journal of Solid State Chemistry,2019,vol. 270,p. 212 - 218

70
[ 89-01-0 ]
lanthanum(III) nitrate hydrated [ No CAS ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7732-18-5 ]
[La2Cd(pyrazine-2,3-dicarboxylate)4(H2O)6]·2H2O}n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; at 120℃; for 96h;High pressure;	General procedure: A mixture of Ln(NO3)3·nH2O (Ln=La, Pr, Nd, Eu, Tb, Dy, Ho, or Er, 0.1mmol), Cd(NO3)2·4H2O (0.15mmol), 2,3-H2pzdc (0.2mmol), H2O (8.0mL), and aqueous solution of NaOH (3.0mL, 0.1molL-1) was added into a Teflon-lined stainless steel bomb at 120C for 96h, and then slowly cooled to room temperature. 1-8 were obtained as strip-shaped crystals and were filtered and dried in air. Elemental analyses (%) calcd. for 1: C, 24.05; H, 2.02; N, 9.35. Found: C, 24.46; H, 2.05; N, 9.18. Calcd. for 2: C, 23.97; H, 2.01; N, 9.32. Found: C, 23.59; H, 2.05; N, 9.19. Calcd. for 3: C, 23.84; H, 2.00; N, 9.27. Found: C, 23.46; H, 2.02; N, 9.15. Calcd. for 4: C, 22.85; H, 2.34; N, 8.88. Found: C, 22.46; H, 2.39; N, 8.69. Calcd. for 5: C, 22.52; H, 2.31; N, 8.75. Found: C, 22.30; H, 2.32; N, 8.83. Calcd. for 6: C, 22.35; H, 2.29; N, 8.69. Found: C, 22.59; H, 2.30; N, 8.48. Calcd. for 7: C, 22.24; H, 2.28; N, 8.64. Found: C, 22.42; H, 2.25; N, 8.47. Calcd. for 8: C, 22.13; H, 2.27; N, 8.60. Found: C, 22.02; H, 2.21; N, 8.42. IR data (KBr, cm-1) for 1-8 were listed in Table S1.