[ CAS No. 5910-89-4 ] {[proInfo.proName]}

Name: 5910-89-4|2,3-Dimethylpyrazine|98%
Brand: Ambeed
SKU: A618688
Price: 5.0 USD
Availability: InStock
Rating: 99 (22 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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3d Animation Molecule Structure of 5910-89-4

Structure of 5910-89-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 5910-89-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5910-89-4 ]

SDS Specification

Alternatived Products of [ 5910-89-4 ]

Product Details of [ 5910-89-4 ]

CAS No. :	5910-89-4	MDL No. :	MFCD00006144
Formula :	C₆H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OXQOBQJCDNLAPO-UHFFFAOYSA-N
M.W :	108.14	Pubchem ID :	22201
Synonyms :

Calculated chemistry of [ 5910-89-4 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	31.96
TPSA :	25.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	0.54
Log Po/w (WLOGP) :	1.09
Log Po/w (MLOGP) :	-0.14
Log Po/w (SILICOS-IT) :	1.81
Consensus Log Po/w :	0.98

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.41
Solubility :	4.25 mg/ml ; 0.0393 mol/l
Class :	Very soluble
Log S (Ali) :	-0.65
Solubility :	24.0 mg/ml ; 0.222 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.36
Solubility :	0.471 mg/ml ; 0.00436 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 5910-89-4 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P312+P330-P303+P361+P353-P304+P340+P312-P305+P351+P338+P310-P332+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501	UN#:	1993
Hazard Statements:	H226-H302-H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 5910-89-4 ]

* 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 [ 5910-89-4 ]
Downstream synthetic route of [ 5910-89-4 ]

[ 5910-89-4 ] Synthesis Path-Upstream 1~49

1
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[ 14331-54-5 ]
[ 694-81-5 ]

Yield	Reaction Conditions	Operation in experiment
5.7%	for 0.0833333 h; Irradiation	General procedure: Irradiation procedure. The dimethylpyrazine or dimethylpyrimidine was placed in a Pyrex tube, attached to the vacuum line, and subjected to three freeze-thaw cycles. The remaining material was then allowed to vaporize into a quartz reaction flask (3 L) that had been evacuated overnight. The resulting pressure in the reaction flask ranged from 1.0 to 1.5 Torr. The flask was irradiated for 5 min. in a Rayonet reaction equipped with either 2, 4,6, 8, or 10 low-pressure 2537 Å Hg lamps.

Reference： [1] Arkivoc, 2017, vol. 2017, # 5, p. 216 - 228

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Reference： [1] Arkivoc, 2017, vol. 2017, # 5, p. 216 - 228

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Reference： [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 22, p. 5364 - 5372

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Kinetics and Catalysis, 2016, vol. 57, # 5, p. 602 - 609[2] Kinet. Katal., 2016, vol. 57, # 5, p. 607 - 614,8

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[ 59489-32-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 465 - 473
[2] Patent: WO2012/89607, 2012, A1,
[3] Patent: WO2007/100670, 2007, A1,

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[ 32493-79-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 465 - 473

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Reference： [1] Journal of Organic Chemistry, 2002, vol. 67, # 2, p. 556 - 565
[2] International Journal of Molecular Sciences, 2018, vol. 19, # 10,

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[ 18433-97-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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[ 5780-66-5 ]

Reference： [1] Kinetics and Catalysis, 2016, vol. 57, # 5, p. 602 - 609[2] Kinet. Katal., 2016, vol. 57, # 5, p. 607 - 614,8

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Reference： [1] Catalysis Communications, 2011, vol. 12, # 12, p. 1067 - 1070

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Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2876 - 2882
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 433 - 450
[3] Patent: US2003/229113, 2003, A1, . Location in patent: Page 20

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Reference： [1] Synthesis, 1984, # 8, p. 676 - 679
[2] Synthesis, 1984, # 8, p. 676 - 679

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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[ 15707-34-3 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708

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Reference： [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 22, p. 5364 - 5372

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Reference： [1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 22, p. 5364 - 5372

[ 5910-89-4 ] Synthesis Path-Downstream 1~88

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[ 5910-89-4 ]
[ 123-38-6 ]
[ 86461-67-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 497 - 500

2
[ 5910-89-4 ]
[ 107427-52-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-Bromosuccinimide; In tetrachloromethane; for 20h;Irradiation; Heating / reflux;	A solution of 10.0 g (93.0 mmol) <strong>[5910-89-4]2,3-dimethylpyrazine</strong> and 70.0 g (390 mmol) N-bromo- succinimide in 800 ml CCI4 is irradiated with a 250 Watt lamp at reflux temperature during 20 hours. After cooling the solution is filtered and the organic phase is washed with a 5% sodium thiosulfate solution and water. After evaporation of the organic phase, the residue is crystallised in ethanol to give 29.1 g (74%) of the title compound, m.p.: 167-1700C.
74%	With N-Bromosuccinimide; In tetrachloromethane; for 20h;Irradiation; Reflux; Inert atmosphere;	(a) A solution of 10.0 g (93.0 mmol) <strong>[5910-89-4]2,3-dimethylpyrazine</strong> and70.0 g (390 mmol) N-bromo-succinimide in 800 ml CCl4 was irradiatedwith a 250 Watt lamp at reflux temperature during 20 h. After cooling the solution was filtered and the organic phase waswashed with a 5% sodium thiosulfate solution and water. Afterevaporation of the organic phase, the residue was crystallized inethanol to give 29.1 g 2,3-bis-dibromomethyl-pyrazine (25) (74%).1H NMR (CDCl3, 400 MHz): 7.1 (s, 2H), 8.6 (s, 2H). MS (electrospray):m/z = 420 [M+1], 422 [M+3], 424 [M+5], 426 [M+7], 428 [M+9]. Mp: 167-170 C.(b) To a solution of 38.0 g (90.0 mmol) 2,3-bis-dibromomethylpyrazine(25) and 70.0 g (400 mmol) diethyl maleate in 450 mlDMF was added 40.0 g (270.0 mmol) NaI and the mixture washeated at 80 C during 20 h. After evaporation of the solvent, theresidue was dissolved in 1000 ml t-butyl-methyl ether and washedwith a 5% sodium thiosulfate solution and water (5 times). Evaporationof the solvent and purification of the residue with flashchromatographygave 9.1 g quinoxaline-6,7-dicarboxylic aciddiethyl ester (26) (37%) as a dark oil.

Reference： [1]Patent: WO2007/20050,2007,A2 .Location in patent: Page/Page column 51
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 403 - 427
[3]European Journal of Inorganic Chemistry,2013,p. 725 - 729
[4]Journal of the Chemical Society. Perkin transactions I,1986,p. 1495 - 1498
[5]Tetrahedron Letters,2010,vol. 51,p. 151 - 152
[6]Chemistry of Materials,2010,vol. 22,p. 6438 - 6443

3
[ 5910-89-4 ]
[ 81831-67-6 ]
[ 51043-75-5 ]

Reference： [1]Synthesis,1984,p. 676 - 679
[2]Synthesis,1984,p. 676 - 679

4
[ 5910-89-4 ]
[ 65464-21-3 ]
[ 38870-37-0 ]

Reference： [1]Synthesis,1985,p. 216 - 217
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 465 - 473

5
[ 54-17-1 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 108-50-9 ]
[ 14667-55-1 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1991,vol. 40,p. 1742 - 1748
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1991,p. 1972 - 1979

6
[ 5910-89-4 ]
[ 7560-50-1 ]
methyl 4-<2-(3-methyl-2-pyrazinyl)ethenyl>cinnamate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 2355 - 2362

7
[ 5910-89-4 ]
[ 41110-28-5 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 556 - 565
[2]International Journal of Molecular Sciences,2018,vol. 19

8
[ 5910-89-4 ]
[ 73183-34-3 ]
2,3-dimethyl-5-(Bpin)-pyrazine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 489 - 491
[2]Organic Letters,2009,vol. 11,p. 3586 - 3589
[3]Organic and Biomolecular Chemistry,2014,vol. 12,p. 7318 - 7327

9
[ 5910-89-4 ]
2,3-dimethyl-6-p-tolylpyrazine 1-oxide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 7781 - 7786

10
[ 5910-89-4 ]
2,3-dimethyl-5-thiophen-2’-yl-pyrazine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 489 - 491
[2]Organic and Biomolecular Chemistry,2014,vol. 12,p. 7318 - 7327

11
[ 5910-89-4 ]
[ 75492-00-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 5994 - 5999

12
[ 5910-89-4 ]
[ 59489-32-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 465 - 473
[2]Patent: WO2012/89607,2012,A1
[3]Patent: WO2007/100670,2007,A1

13
[ 5910-89-4 ]
[ 32493-79-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 465 - 473

14
[ 5910-89-4 ]
[ 84468-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In ethanol; under 2844.39 - 3102.97 Torr; for 72h;	2.56 g of 2,3-dimethyl-pyrazine (23.67 mmol) was dissolved in 100 mL of ethanol with 2.1 g 10% palladium on active carbon. The reaction mixture was hydrogenated under pressure (55-60 psi) for 3 days. The solid was filtered and removed. The filtrate was concentrated to afford 3.0 g of 2,3-dimethylpiperazine, which was used without purification. 1H NMR (400 MHz, CDCl3), delta (ppm): 2.95 (m, 4H), 2.74 (m, 2H), 1.04 (d, 6H).

Reference： [1]Patent: US2005/234046,2005,A1 .Location in patent: Page/Page column 75

15
[ 5910-89-4 ]
[ 165184-98-5 ]
[ 145413-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium diisopropyl amide; In tetrahydrofuran;	EXAMPLE III 2-(3-Hexyl-2-hydroxy-4-phenyl-3-buten-1-yl)-3-methylpyrazine STR11 To a solution of lithium diisopropylamide (1.5 Molar, 73.3 mL, 0.11 mole) in 150 mL of tetrahydrofuran at -78 C. is added slowly to a solution of <strong>[5910-89-4]2,3-dimethylpyrazine</strong> (10.8 g, 0.1 mole) in 100 mL of tetrahydrofuran. The mixture is allowed to warm to room temperature and then cooled to -78 C. A solution of alpha-hexylcinnamaldehyde (23.7 g, 0.11 mole) in 100 mL of tetrahydrofuran is added dropwise over 15 minutes. The reaction product mixture is then worked up according to the procedures of Example I to provide the title compound.

Reference： [1]Patent: US5218118,1993,A

16
[ 5910-89-4 ]
[ 25513-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With selenium(IV) oxide; In ethyl acetate; at 70℃; for 2.0h;diatomaceous earth;	A mixture of 2,3-dimethylpyrazine (2Og, 18.5mmol), selenium dioxide (41.06g, 37mmol) and diatomeous earth (2Og) in EtOAc (500ml) was stirred and heated at 7O0C for 2 hours. The mixture was allowed to cool and the insoluble matter was removed by filtration EPO <DP n="112"/>through diatomeous earth. The filtrate was washed with saturated aqueous sodium hydrogen carbonate solution and then saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was suspended in water (100ml) and hydroxylamine (45ml of a 50% aqueous solution) was added. The mixture was stirred at ambient temperature for 18 hours and the mixture then extracted with EtOAc. The extracts were combined, washed with saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with isohexane to give 3- methylpyrazine-2-carboxaldehyde oxime (9.65g, 38%); NMR Spectrum 2.67 (s, 3H), 8.23 (s, IH), 8.45-8.49 (m, 2H), 11.87 (s, IH).
	With selenium(IV) oxide; In ethyl acetate; at 70℃; for 2.0h;	The S-2-[3-(3-methylpyrazin-2-yl)isoxazol-5-yl]pyrrolidine starting material was prepared as follows: A mixture of 2,3-dimethylpyrazine (2Og, 18.5mmol), selenium dioxide (41.06g,25 37mmol) and diatomeous earth (2Og) in EtOAc (500ml) was stirred and heated at 7O0C for 2 hours. The mixture was allowed to cool and the insoluble matter was removed by filtration through diatomeous earth. The filtrate was washed with saturated aqueous sodium hydrogen carbonate solution and then saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was suspended in water (100ml) and30 hydroxylamine (45ml of a 50% aqueous solution) was added. The mixture was stirred at ambient temperature for 18 hours and the mixture then extracted with EtOAc. The extracts were combined, washed with saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with isohexane to give 3- EPO <DP n="89"/>methylpyrazine-2-carboxaldehyde oxime (9.65g, 38%); NMR Spectrum 2.67 (s, 3H), 8.23 (s, IH), 8.45-8.49 (m, 2H), 11.87 (s, IH).
	With selenium(IV) oxide; In ethyl acetate; at 70℃; for 2.0h;diatomeous earth;	A mixture of 2,3-dimethylpyrazine (2Og, 18.5mmol), selenium dioxide (41.06g, 37mmol) and diatomeous earth (2Og) in EtOAc (500ml) was stirred and heated at 700C for 220 hours. The mixture was allowed to cool and the insoluble matter was removed by filtration through diatomeous earth. The filtrate was washed with saturated aqueous sodium hydrogen carbonate solution and then saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was suspended in water (100ml) and hydroxylamine (45ml of a 50% aqueous solution) was added. The mixture was stirred at25 ambient temperature for 18 hours and the mixture then extracted with EtOAc. The extracts were combined, washed with saturated aqueous sodium chloride solution, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with isohexane to give 3- methylpyrazine-2-carboxaldehyde oxime (9.65g, 38%); NMR Spectrum 2.67 (s, 3H), 8.23 (s, IH), 8.45-8.49 (m, 2H), 11.87 (s, IH).

Reference： [1]Patent: WO2006/106307,2006,A1 .Location in patent: Page/Page column 110-111
[2]Patent: WO2006/109026,2006,A1 .Location in patent: Page/Page column 87-88
[3]Patent: WO2006/100461,2006,A1 .Location in patent: Page/Page column 94

17
[ 5910-89-4 ]
[ 590-12-5 ]
dimeric pyrazine [ No CAS ]
[ 75907-71-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium diisopropyl amide; In water;	Method B To a solution of 0.1 mole of lithium diisopropylamide in 150 milliliters of ether at 0 C., under nitrogen, was added a solution of 10.8 grams (0.1 mole) of <strong>[5910-89-4]2,3-dimethylpyrazine</strong> in 50 milliliters of ether. The mixture was stirred for 20 minutes, and a solution of 18.6 grams (0.1 mole) of 1,2-dibromoethylene in 40 milliliters of ether was added at 0 C. Stirring was continued for 40 minutes, after which period water was added. The ether layer was separated and the aqueous layer was extracted first with ether and then with methylene chloride. The combined organic exerts were dried over magnesium sulfate and the solvent was removed to yield 21 grams of crude product. One gram of the crude mixture was subjected to preparative thin layer chromatography and there was obtained 280 mg (55%) of the dimeric pyrazine. Recrystallization from hexane gave plates, m.p. 94-96 C.

Reference： [1]Patent: US4620004,1986,A

18
[ 5910-89-4 ]
[ 282528-30-7 ]

Yield	Reaction Conditions	Operation in experiment
36%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane;Inert atmosphere;	Compound 2 was synthesized as described previously from <strong>[5910-89-4]2,3-dimethylpyrazine</strong> (1) resulting in comparable yields and identical NMR spectra [37].1H NMR (400 MHz, CDCl3) delta=8.43 (s, 2H), 4.65 (s, 4H); 13C NMR (125 MHz, CDCl3)=151.4, 143.9, 29.5.
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 16h;Heating / reflux;	Part A:Under argon, the compound <strong>[5910-89-4]2,3-dimethylpyrazine</strong> (216 mg, 2.0 mmol) was dissolved in CCI4 (10 mL), 2,2'-azobis(2-methylpropionitrile) (33 mg, 0.2 mmol) and NBS (356 mg, 2.0 mmol) were added. The mixture was refluxed for 16 <n="90"/>hours. The mixture was filtered and washed with CCU. The filtrate was concentrated and purified with column (silica gel, EtOAc) gave the product 60 (457 mg) as yellow solid. HPLC-MS tR = 1.34 min (UV254 nm); mass calculated for formula C6H6Br2N2 263.9, observed LCMS m/z 264.9 (M+H).
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 16h;Heating / reflux;	To a solution of <strong>[5910-89-4]2,3-dimethylpyrazine</strong> (1.33 g, 12.3 mmol) in tetrachloromethane (30 mL) was added N-bromosuccinimide (6.6 g, 37 mmol)) and 2,2'-azobis(2-methylprorhoionitrile) (0.2 g, 1.2 mmol). After refluxing under nitrogen for 16 h7 the mixture was filtered, and washed with tetrachloromethane. The filtrate was concentrated, and the residue was purified on Biotage silica gel cartridge (gradient 2-20% ethyl acetate in hexanes) to yield 2,3-di(bromomethyl)pyrazine. A solution of 2,3-di(brornomethyl)pyrazine (2.0 g, 7.7 mmol) in iV,N-dimethylformamide (100 mL) at 0 0C was mixed with a solution of tritylarnine (6.0 g, 23.0 mmol) in 7/,N-dimethylformamide. The resulting mixture was stirred at room temperature for one h, heated at 60 0C for 3 h, and then poured into water and extracted with ethyl acetate (2 x 200 mL). The organic layers were washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified on Biotage silica gel cartridge (gradient 2-50% ethyl acetate in hexanes) to yield the nu-trityl-pyrrolopyrazine. A portion of this product (420 mg, 1.2 mmol) was treated with 4nu of hydrochloric acid in methanol for 2 h. After solvent was removed, the residue was purified on Biotage silica gel cartridge (gradient 0-12% methanol containing 1% ammonium hydroxide in dichloromethane) to yield Intermediate 17.

Reference： [1]Chemical Communications,2014,vol. 50,p. 9591 - 9594
[2]Patent: US2015/376591,2015,A1 .Location in patent: Paragraph 0174-0176
[3]Patent: WO2009/14637,2009,A2 .Location in patent: Page/Page column 88-89
[4]Patent: WO2007/97931,2007,A2 .Location in patent: Page/Page column 36

19
[ 5910-89-4 ]
copper(II) perchlorate hexahydrate [ No CAS ]
tris(2,3-dimethylpyrazino)dicopper(I) perchlorate [ No CAS ]

Reference： [1]Polyhedron,1993,vol. 12,p. 1019 - 1026
[2]Polyhedron,1991,vol. 10,p. 1835 - 1838
[3]Polyhedron,1991,vol. 10,p. 1835 - 1838

20
[ 5910-89-4 ]
silver hexafluoroantimonate [ No CAS ]
2Ag⁽¹⁺⁾*3C₄H₂N₂(CH₃)2*2SbF₆^(1-) = [Ag₂(C₄H₂N₂(CH₃)2)3](SbF₆)2 [ No CAS ]

Reference： [1]Chemical Communications,1996,p. 1393 - 1394

21
[ 5910-89-4 ]
silver carbonate [ No CAS ]
[ 121-57-3 ]
[Ag(p-aminobenzenesulfonato)(2,3-dimethylpyrazine)] [ No CAS ]

Reference： [1]Inorganic Chemistry,2007,vol. 46,p. 7299 - 7311

22
[ 5910-89-4 ]
[ 81-05-0 ]
[ 7732-18-5 ]
silver carbonate [ No CAS ]
[Ag(6-amino-1-naphthalenesulfonato)(2,3-dimethylpyrazine)]*1.5H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry,2007,vol. 46,p. 7299 - 7311

23
[ 5910-89-4 ]
dodecatungstosilic acid [ No CAS ]
copper(II) nitrate trihydrate [ No CAS ]
([Cu(2,3-dimethylpyrazine)1.5]4(SiW₁₂O₄₀))n [ No CAS ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 10702 - 10711

24
[ 5910-89-4 ]
[ 32315-10-9 ]
[ 100-47-0 ]
[ 1202924-79-5 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 5738 - 5743

25
[ 50-99-7 ]
[ 134276-45-2 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-03-6 ]