[ CAS No. 141-90-2 ] {[proInfo.proName]}

Name: 141-90-2|4-Hydroxypyrimidine-2(1H)-thione|97%
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Quality Control of [ 141-90-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 141-90-2 ]

SDS Specification

Alternatived Products of [ 141-90-2 ]

Product Details of [ 141-90-2 ]

CAS No. :	141-90-2	MDL No. :	MFCD00006039
Formula :	C₄H₄N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZEMGGZBWXRYJHK-UHFFFAOYSA-N
M.W :	128.15	Pubchem ID :	1269845
Synonyms :	Thiouracil;Antagothyroil;NSC 290414;NSC 290413;NSC 290412;NSC 19473	Chemical Name :	4-Hydroxypyrimidine-2(1H)-thione

Calculated chemistry of [ 141-90-2 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	31.44
TPSA :	81.0 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) :	-7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.93
Log Po/w (XLOGP3) :	-0.05
Log Po/w (WLOGP) :	0.84
Log Po/w (MLOGP) :	-0.81
Log Po/w (SILICOS-IT) :	2.18
Consensus Log Po/w :	0.62

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.16
Solubility :	8.91 mg/ml ; 0.0695 mol/l
Class :	Very soluble
Log S (Ali) :	-1.2
Solubility :	8.08 mg/ml ; 0.063 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.15
Solubility :	9.11 mg/ml ; 0.0711 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.7

Safety of [ 141-90-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P201-P202-P281-P308+P313-P405-P501	UN#:	N/A
Hazard Statements:	H303-H351	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 141-90-2 ]

* 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 [ 141-90-2 ]
Downstream synthetic route of [ 141-90-2 ]

[ 141-90-2 ] Synthesis Path-Upstream 1~19

1
[ 141-90-2 ]
[ 611-08-5 ]

Reference： [1] American Chemical Journal, 1905, vol. 33, p. 443

2
[ 141-90-2 ]
[ 7697-37-2 ]
[ 611-08-5 ]

Reference： [1] American Chemical Journal, 1905, vol. 33, p. 443

3
[ 141-90-2 ]
[ 3934-20-1 ]

Reference： [1] Journal of Biological Chemistry, 1907, vol. 2, p. 114[2] Chem. Zentralbl., 1906, vol. 77, # II, p. 1508

4
[ 141-90-2 ]
[ 10026-13-8 ]
[ 3934-20-1 ]

Reference： [1] Journal of Biological Chemistry, 1907, vol. 2, p. 114[2] Chem. Zentralbl., 1906, vol. 77, # II, p. 1508

5
[ 17356-08-0 ]
[ 141-90-2 ]

Yield	Reaction Conditions	Operation in experiment
4.25 g	Stage #1: at 60℃; for 2 h; Stage #2: With hydrogenchloride In water for 1 h;	Thiourea (0.045 mol, 3.42 g) was weighed out,Crushed into the crude product obtained in Example 1,The reaction solution becomes thick, diluted with 15mL ethyl acetate reaction system,The reaction was stirred at 60 ° C for 2 hours and the reaction was completed by TLC.The reaction was concentrated to dryness,The resulting white solid was added 40mL hydrochloric acid solution (3mol / L) pulping 1 hour after filtration,Filter cake with 10mL water rinse,50 ° C for 4 hours under vacuum to give a white solid powder 4.25g,Two-step combined yield of 74percent, purity: 98.97percent.

Reference： [1] Patent: CN106928152, 2017, A, . Location in patent: Paragraph 0010; 0022; 0023; 0024

6
[ 333-49-3 ]
[ 141-90-2 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 23, p. 3611 - 3617

7
[ 1257309-84-4 ]
[ 141-90-2 ]
[ 2655-79-0 ]

Reference： [1] Nucleosides, Nucleotides and Nucleic Acids, 2010, vol. 29, # 10, p. 768 - 785

8
[ 17356-08-0 ]
[ 122-51-0 ]
[ 141-90-2 ]

Reference： [1] Journal of Organic Chemistry, 2002, vol. 67, # 19, p. 6731 - 6737

9
[ 20235-78-3 ]
[ 141-90-2 ]

Reference： [1] Nucleosides, Nucleotides and Nucleic Acids, 2017, vol. 36, # 2, p. 107 - 121

10
[ 10601-80-6 ]
[ 17356-08-0 ]
[ 141-90-2 ]

Reference： [1] Journal of the American Chemical Society, 1950, vol. 72, p. 2587,2593

11
[ 75039-91-7 ]
[ 141-90-2 ]
[ 598-52-7 ]
[ 33238-58-3 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 7, p. 1872 - 1877

12
[ 13233-20-0 ]
[ 141-90-2 ]
[ 333-49-3 ]
[ 20235-78-3 ]

Reference： [1] Nature Chemistry, 2017, vol. 9, # 4, p. 303 - 309

13
[ 87769-48-0 ]
[ 17356-08-0 ]
[ 141-90-2 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1986, vol. 34, # 2, p. 621 - 627

14
[ 666713-60-6 ]
[ 17356-08-0 ]
[ 141-90-2 ]

Reference： [1] Archiv der Pharmazie, 1984, vol. 317, # 5, p. 425 - 430

15
[ 6965-19-1 ]
[ 141-90-2 ]

Reference： [1] American Chemical Journal, 1908, vol. 40, p. 557

16
[ 874-14-6 ]
[ 17356-08-0 ]
[ 141-90-2 ]

Reference： [1] Heterocycles, 1984, vol. 21, # 1, p. 289 - 307

17
[ 7424-91-1 ]
[ 17356-08-0 ]
[ 141-90-2 ]

Reference： [1] Synthesis, 1986, # 12, p. 1041 - 1044

18
[ 98484-57-2 ]
[ 141-90-2 ]

Reference： [1] Journal of the Chemical Society, 1958, p. 153,155

19
[ 89693-81-2 ]
[ 141-90-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 10, p. 2221 - 2226

[ 141-90-2 ] Synthesis Path-Downstream 1~88

1
[ 141-90-2 ]
[ 74-88-4 ]
[ 5751-20-2 ]

Yield	Reaction Conditions	Operation in experiment
100%		(EX-6A) 2-Thiouracil (66.7 g, 520.5 mmol) was dissolved in a sodium hydroxide solution (41.6 g of solid NaOH in 365 mL of water). The mixture was then treated with methyl iodide (37 mL, 583 mmol), and the resulting reaction mixture was allowed to stir for 16 h at room temperature. The solution was then acidified with glacial acetic acid (30 mL). The white precipitate was collected by suction filtration, and the solid was washed several times with cold water and dried to afford 74 g of EX-6A as a white crystalline solid in quantitative yield.
99%	With sodium hydroxide; at 20℃; for 18h;	Step 1: 2-(Methylthio)pyrimidin-4(3H)-one 2-Thiouracil (1) (5 g, 39 mmol) was dissolved in sodium hydroxide (2.91 M, 26.8 mL). Methyl iodide (2.73 mL, 43.7 mmol) was added and the mixture was stirred at room temperature for 18 h. 300 mL of a 3 M HCI solution was added and the methanol was evaporated. Then the reaction mixture was cooled to 0°C and acidified to a pH of 4 using glacial acetic acid. The precipitate was filtered and washed with water and dried to give the title compound (4.74 g, 99percent) as a white solid. 1H NMR (CD3OD) delta 7.84 (d, J= 6.4 Hz, 1H), 6.1 1 (d, J= 6.4 Hz, 1H), 4.90 (br s, 2H), 2.55 (s, 3H); LCMS (Condition B): 0.89 min, 165 (M+Na).
95%	With sodium hydroxide; In water; at 20℃; for 16h;	2-Thiouracile (10 g, 0.078 mol) was mixed with aq. solution of sodium hydroxide (6.24 g in 55 mL of water), then methyl iodide (5.5 mL, 0.088 mol) was added. The resulting mixture was stirred at ambient temperature for 16 h. The resulting solution was acidified with glacial acetic acid (4.5 mL), formed crystals were filtered, washed with cold water and air-dried to give 2-(methylsulfanyl)pyrimidin-4(3H)-one. Yield 10.5 g (95percent); colorless solid; mp 196?197 °C; 1 H NMR (400 MHz, DMSO-d 6 ): delta 7.85 (d, J = 7.5 Hz, 1), 6.08 (d, J = 7.5 Hz, 1), 2.45 (s, 3). Mixture of 2-(methylsulfanyl)pyrimidin-4(3H)-one (4.3 g, 0.03 mol), iodine (9.15 g, 0.036 mol), sodium hydroxide (1.5 g, 0.037 mol) and water (23 ml) was stirred at 80 ° for 7 h. After neutralization with acetic acid the resulting precipitate was filtered and recrystallized from ethanol to give 5-iodo-2-(methylsulfanyl)pyrimidin-4(3H)-one. Yield 6.98 g (87percent); colorless solid; mp 210?211 °C (decomp.); 1 H NMR (400 MHz, DMSO-d 6 ): delta 8.31 (s, 1), 2.46 (s, 3). Mixture of 5-iodo-2-(methylsulfanyl)pyrimidin-4(3H)-one (6.98 g, 0.026 mol) and phosphorus oxychloride (12 ml, 0.13 mol) was refluxed during 3 h. Reaction mixture was poured into crushed ice, the resulting precipitate was filtered, washed with cold water and air-dried to give compound 3a. Yield 6.94 g (93percent); colorless solid; mp 60?62 °C (lit. [9] mp 63?64 °); 1 H NMR (400 MHz, CDCl 3 ): delta 8.69 (s, 1), 2.55 (s, 3).

81%		2a) 2-THIOMETHVL-URACIL To a suspension of 2-thiouracil (78.00 g, 0.609 mol) in water (160 mL) and isopropanol (80 mL) cooled to 0-5°C is added dropwise a 30percent sodium hydroxide solution (48.7 g, 1.22 mol : in water 160 mL). A solution of methyl iodide (41.7 mL, 0.669 mol) in isopropanol (150 mL) is added dropwise over 2 hours. The mixture is allowed to warm to room temperature and is stirred for 1 hour. The mixture is concentrated to half volume in vacuo, cooled to 5°C and then acidified to pH 6.5 with concentrated HCI. The solid precipitate is collected by filtration, washed with cold water and dried in vacuo to give 70 g white solid (81percent). M+H1 = 142. 'H NMR (DMSO); 8 12.8 (bs, 1H), 7.90 (d, LHJ, 6. 07 (d, 1H), 2.37 (s, 3H).
54%		2-thioxo-2,3-dihydropyrimidin-4(1 H)-one (66.7 g, 0.497 mol) was dissolved in aq.NaOH (41 .6 g of solid in 365 ml_ of H2O). The mixture was then treated with CH3I (100.1 g, 0.704 mol) and was stirred at room temperature for 18 h. TLC (petroleum ether: EtOAc=4:1 ) indicated that the reaction was complete. The resulting mixture was adjusted to pH=5~6 with HOAc (30 ml_). The solid formed was collected and dried on vacuum to give title compound (40 g, 54percent) as a white solid.
	With sodium hydroxide;	Example 11 Synthetic route
	With sodium hydroxide;	Example 11 Synthetic route
28 g	With sodium hydroxide; In water; at 10 - 35℃;	A) 2-(methylsulfanyl)pyrimidin-4(3H)-one To an aqueous solution (200 mL) of sodium hydroxide (23 g) were added 2-thioxo-2,3-dihydropyrimidin-4(1H)-one (37 g) and iodomethane (20 mL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added acetic acid (17 mL), and the precipitate was collected by filtration, and washed with ice water. The residue was dried to give the title compound (28 g). 1H NMR (400 MHz, DMSO-d6) delta 2.48 (3H, s), 6.10 (1H, d, J = 6.6 Hz), 7.87 (1H, d, J = 6.4 Hz), 12.69 (1H, brs).

Reference： [1]Patent: US6653316,2003,B1 .Location in patent: Page/Page column 117-118
[2]Tetrahedron,2010,vol. 66,p. 1280 - 1288
[3]Patent: WO2014/58685,2014,A1 .Location in patent: Page/Page column 41
[4]Synthesis,2016,vol. 48,p. 2851 - 2862
[5]Synthetic Communications,1997,vol. 27,p. 1943 - 1949
[6]Synlett,2012,vol. 23,p. 1305 - 1308
[7]Patent: WO2005/28444,2005,A1 .Location in patent: Page/Page column 49
[8]Journal of Organic Chemistry,1993,vol. 58,p. 807 - 808
[9]Patent: WO2012/52948,2012,A1 .Location in patent: Page/Page column 52
[10]Journal of the American Chemical Society,1948,vol. 70,p. 1753,1755
[11]Archiv der Pharmazie,1984,vol. 317,p. 425 - 430
[12]Patent: WO2011/130908,2011,A1 .Location in patent: Page/Page column 54-55
[13]Patent: WO2011/133444,2011,A1 .Location in patent: Page/Page column 53-54
[14]Patent: EP2832734,2015,A1 .Location in patent: Paragraph 0766

2
[ 512-56-1 ]
[ 141-90-2 ]
[ 5751-20-2 ]

Reference： [1]Synthetic Communications,1980,vol. 10,p. 791 - 798

3
[ 512-56-1 ]
[ 141-90-2 ]
[ 5751-20-2 ]
[ 6327-98-6 ]
[ 6330-98-9 ]
[ 76541-59-8 ]

Reference： [1]Synthetic Communications,1980,vol. 10,p. 791 - 798

4
[ 512-56-1 ]
[ 141-90-2 ]
[ 5751-20-2 ]
[ 6327-98-6 ]
[ 6330-98-9 ]
[ 1194-71-4 ]

Reference： [1]Synthetic Communications,1980,vol. 10,p. 791 - 798

5
5-(dihydroxyboryl)-1,3-dimethyluracil [ No CAS ]
[ 141-90-2 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 315 - 319

6
[ 3034-48-8 ]
[ 141-90-2 ]
[ 79134-08-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1981,vol. 16,p. 233 - 239

7
[ 141-90-2 ]
[ 3131-52-0 ]
2-(5,6-Dihydroxy-1H-indol-2-ylsulfanyl)-3H-pyrimidin-4-one [ No CAS ]
2-(5,6-Dihydroxy-1H-indol-3-ylsulfanyl)-3H-pyrimidin-4-one [ No CAS ]
5,5',6,6'-tetrahydroxy-2,2'-bis[(4-hydroxypyrimidin-2-yl)thio]-4,4'-biindolyl [ No CAS ]
5,5',5",6,6',6"-hexahydroxy-2',3-bis[(4-hydroxypyrimidin-2-yl)thio]4,7':4',4"-terindolyl [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 5192 - 5201
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 5192 - 5201

8
[ 141-90-2 ]
[ 7697-37-2 ]
[ 611-08-5 ]

Reference： [1]American Chemical Journal,1905,vol. 33,p. 443

9
[ 25542-62-5 ]
[ 141-90-2 ]
[ 912956-59-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4656 - 4661

10
[ 141-90-2 ]
[ 932-52-5 ]
5-(4-hydroxy-pyrimidin-2-ylsulfanyl)-1<i>H</i>-pyrimidine-2,4-dione [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2006,vol. 45,p. 980 - 985

11
[ 141-90-2 ]
[ 74-88-4 ]
[ 5751-20-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	In water; at 20℃; for 24h;	A mixture of methyl iodide (66 g, 0.47 mol) and 2-mercaptopyrimin-4-ol (50 g, 0.39 mol) in water (500 mL) was stirred at room temperature for 24 h then acetic acid was added to acidify the reaction mixture. The resultant precipitate was collected by filtration, washed with water and dried in vacuo to afford 2-(methylthio)pyrimidin-4-ol (40 g, 72% yield) as a white solid.
	With sodium hydroxide; In water; at 20℃; for 24h;	Stage 1: 2-(Methylthio)pyrimidin-4-ol: To a mixture containing 100 g of commercial 2-thiopyrimidin-4-ol, 60 g of sodium hydroxide in 800 ml of water, are added dropwise 38 ml of methyl iodide. The reaction medium is kept stirring at room temperature for 24 hours. The solution is acidified with 135 ml of acetic acid and left for 24 hours in a refrigerator. The white precipitate is filtered and washed several times with cold water. After drying, 60 g of expected compound are obtained.
		38 ml of methyl iodide are added dropwise to a mixture comprising 100 g of commercial 2-thiopyrimidin-4-ol and 60 g of sodium hydroxide in 800 ml of water. The reaction mixture is left stirring at AT for 24 h. The solution is acidified with 135 ml of acetic acid and left in a refrigerator for 24 h. The white precipitate is filtered off and washed several times with cold water. After drying, 60 g of the expected compound are obtained.

		2-(Methylthio)pyrimidin-4-ol Added dropwise to a mixture containing 100 g of commercial 2-thiopyrimidin-4-ol, 60 g of sodium hydroxide in 800 ml of water were 38 ml of methyl iodide. The reaction mixture was left stirring at ambient temperature for 24 hours. The solution was acidified with 135 ml of acetic acid and left for 24 hours in a refrigerator. The white precipitate was filtered and washed several times with cold water. After drying, 60 g of the target compound was obtained.
	With sodium hydroxide; In ethanol; water; at 30 - 70℃; for 0.333333h;	A mixture of compound 1 (1.28 gm) and NaOH (0.43 gm) was suspended in water (6 ml) and heated to 60-70C until the solids were dissolved. Ethanol (7 ml) and methyl iodide (Mel) (0.63 ml) were added after the solution being cooled to about 30C. The solution was then again heated to 50-60C for 20 min, and then cooled to room temperature on which, white solid precipitated from the solution and it was collected by filtration. The washings were acidified with acetic acid, and the excess solvent was removed in vacuum until precipitation of white solid was observed. After filtration, the combined precipitates were thoroughly washed with water and recrystallized from ethanol to yield compound 2.

Reference： [1]Patent: WO2013/174895,2013,A1 .Location in patent: Page/Page column 64
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 1146 - 1157
[3]Patent: US2008/269170,2008,A1 .Location in patent: Page/Page column 67
[4]Patent: US2010/69417,2010,A1 .Location in patent: Page/Page column 20
[5]Patent: US2010/99694,2010,A1 .Location in patent: Page/Page column 20-21
[6]Patent: WO2018/92034,2018,A1 .Location in patent: Paragraph 0074

12
[ 141-90-2 ]
[ 74-88-4 ]
[ 5751-20-2 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium hydroxide; In ethanol; water; at 30 - 60℃; for 0.333333h;	A mixture of 12.8 g (99.9 mmol) of 2-thiouracil and 4.3 g (108 mmol) of sodium hydroxide was placed in 500ml Erlenmeyer flask, and dissolved on the oil bath with a minimum amount of water. Twice the volume of 99percent ethanol was then added, the solution cooled to 30°C, and 6.3 ml (99.9 mmol) of methyl iodide added. The solution was heated to 60°C for 20 min, then cooled to room temp. The precipitate was filtered off, and, after acidifying the filtrate with acetic acid, the excess solvent was removed in vacuo. The combined precipitates were thoroughly washed with water and recrystallized from ethanol to give 6.0g (47percent) of product. 1H NMR (CDC13) 5: 2 .59 (s, 3H) , 6.23 (d, J = 6.7 Hz, 1H) , 7.89 (d, J = 6.4 Hz, 1H) .
		20g (153 mmol) 2-thiouracil are suspended in 250 mL MeOH and then 8.7 g (152.9 mmol, 1 eq) sodium methoxide are added. The solution is stirred for 5 min at RT and then 12.4 mL (198.8 mmol, 1.3 eq) methyl iodide are added dropwise. The reaction mixture is stirred overnight, then poured onto water and extracted 3.x. with approx. 150 mL chloroform. The combined organic phases are dried on MgSO4, the solvent is eliminated in vacuo and 16g E-1 are obtained.

Reference： [1]Patent: WO2005/99688,2005,A2 .Location in patent: Page/Page column 172-173
[2]Patent: US2009/163467,2009,A1 .Location in patent: Page/Page column 18

13
[ 109-70-6 ]
[ 141-90-2 ]
C₇H₉ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 12

14
[ 109-70-6 ]
[ 141-90-2 ]
C₇H₉ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 26

15
[ 54512-75-3 ]
[ 141-90-2 ]
C₉H₁₃ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 5

16
[ 107-04-0 ]
[ 141-90-2 ]
C₆H₇ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

17
[ 141-90-2 ]
[ 193607-69-1 ]

Reference： [1]Patent: US6352981,2002,B1 .Location in patent: Page column 16-17

18
C₁₆H₂₂ClF₃N₂ [ No CAS ]
[ 141-90-2 ]
C₂₀H₂₅F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 5

19
C₁₅H₂₀ClF₃N₂ [ No CAS ]
[ 141-90-2 ]
C₁₉H₂₃F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 6

20
[ 6974-77-2 ]
[ 141-90-2 ]
C₈H₁₁ClN₂O₂S [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 6

21
C₁₅H₁₈ClF₃N₂ [ No CAS ]
[ 141-90-2 ]
C₁₉H₂₁F₃N₄OS*2ClH [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

22
C₁₆H₁₉ClF₆N₂ [ No CAS ]
[ 141-90-2 ]
C₂₀H₂₂F₆N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 17

23
C₁₄H₂₁ClN₂O₂S [ No CAS ]
[ 141-90-2 ]
C₁₈H₂₄N₄O₃S₂ [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 18

24
[ 454228-70-7 ]
[ 141-90-2 ]
C₁₉H₂₀F₃N₃OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 19

25
[ 454228-70-7 ]
[ 141-90-2 ]
C₁₉H₂₀F₃N₃OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 28

26
C₁₅H₁₉ClF₃N [ No CAS ]
[ 141-90-2 ]
C₁₉H₂₂F₃N₃OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 20

27
C₁₄H₁₇ClF₃N₃ [ No CAS ]
[ 141-90-2 ]
C₁₈H₂₀F₃N₅OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 21

28
C₁₃H₁₇Cl₃N₂ [ No CAS ]
[ 141-90-2 ]
C₁₇H₂₀Cl₂N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 23

29
[ 6294-17-3 ]
[ 141-90-2 ]
C₁₀H₁₅ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 24

30
1-(6-Chlorohexyl)-4-(3-trifluoromethylphenyl)piperazine [ No CAS ]
[ 141-90-2 ]
C₂₁H₂₇F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 24

31
[ 454228-78-5 ]
[ 141-90-2 ]
C₁₉H₂₂F₃N₃OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 25

32
[ 454228-78-5 ]
[ 141-90-2 ]
C₁₉H₂₂F₃N₃OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 26

33
C₁₅H₁₇ClF₆N₂ [ No CAS ]
[ 141-90-2 ]
C₁₉H₂₀F₆N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 30

34
C₁₄H₁₇BrClF₃N₂ [ No CAS ]
[ 141-90-2 ]
C₁₈H₂₀BrF₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

35
C₁₉H₂₃ClN₂ [ No CAS ]
[ 141-90-2 ]
C₂₃H₂₆N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

36
C₁₃H₁₈ClIN₂ [ No CAS ]
[ 141-90-2 ]
C₁₇H₂₁IN₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

37
[ 175157-09-2 ]
[ 141-90-2 ]
C₁₈H₂₂F₂N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

38
C₁₇H₂₇ClN₂ [ No CAS ]
[ 141-90-2 ]
C₂₁H₃₀N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

39
C₂₁H₃₅ClN₂ [ No CAS ]
[ 141-90-2 ]
C₂₅H₃₈N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

40
[ 57061-71-9 ]
[ 141-90-2 ]
C₁₇H₁₉F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

41
C₁₃H₁₇ClF₃N₃ [ No CAS ]
[ 141-90-2 ]
C₁₇H₂₀F₃N₅OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

42
1-(4-chloro-3-(trifluoromethyl)phenyl)-4-(3-chloropropyl) piperazine [ No CAS ]
[ 141-90-2 ]
C₁₈H₂₀ClF₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

43
C₂₂H₂₈ClF₃N₄ [ No CAS ]
[ 141-90-2 ]
A-437203 [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

44
C₁₂H₁₉ClN₄O₂ [ No CAS ]
[ 141-90-2 ]
C₁₆H₂₂N₆O₃S [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

45
C₁₉H₂₀Cl₂F₃N₃ [ No CAS ]
[ 141-90-2 ]
C₁₇H₁₉ClF₃N₅OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

46
C₄H₆BrCl [ No CAS ]
[ 141-90-2 ]
C₈H₉ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

47
C₂₃H₂₈ClF₃N₄ [ No CAS ]
[ 141-90-2 ]
C₂₁H₂₇F₃N₆OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

48
C₁₆H₂₅ClN₂ [ No CAS ]
[ 141-90-2 ]
C₂₀H₂₈N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

49
C₂₂H₂₆ClN₅ [ No CAS ]
[ 141-90-2 ]
C₂₀H₂₅N₇OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

50
[ 141-90-2 ]
[ 185202-54-4 ]
C₂₁H₂₄N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

51
C₁₄H₁₇Cl₃N₂ [ No CAS ]
[ 141-90-2 ]
C₁₈H₂₀Cl₂N₄OS*ClH [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Page column 1

52
C₂₀H₂₃ClN₂ [ No CAS ]
[ 141-90-2 ]
C₂₄H₂₆N₄OS*ClH [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

53
C₁₅H₂₁ClF₃N₃ [ No CAS ]
[ 141-90-2 ]
C₁₉H₂₄F₃N₅OS*Cl^(1-) [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

54
[ 141-90-2 ]
[ 66323-17-9 ]
C₉H₁₁ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

55
C₁₆H₂₀ClF₃N₂ [ No CAS ]
[ 141-90-2 ]
C₂₀H₂₃F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

56
[ 68105-93-1 ]
[ 141-90-2 ]
C₁₁H₁₇ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

57
C₁₈H₂₆ClF₃N₂ [ No CAS ]
[ 141-90-2 ]
C₄H₄O₄*C₂₂H₂₉F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

58
[ 28598-82-5 ]
[ 141-90-2 ]
C₁₂H₁₉ClN₂OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

59
C₁₉H₂₈ClF₃N₂ [ No CAS ]
[ 141-90-2 ]
C₄H₃O₄^(1-)*C₂₃H₃₁F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

60
C₁₈H₂₇ClN₂ [ No CAS ]
[ 141-90-2 ]
C₂₁H₂₈N₄OS*2Cl^(1-) [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

61
[ 78056-40-3 ]
[ 141-90-2 ]
C₁₈H₂₁F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 12

62
[ 78056-40-3 ]
[ 141-90-2 ]
C₁₈H₂₁F₃N₄OS [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Example 27

63
[ 78056-40-3 ]
[ 141-90-2 ]
C₁₈H₂₁F₃N₄OS*Cl^(1-) [ No CAS ]

Reference： [1]Patent: US6342604,2002,B1 .Location in patent: Table 1

64
[ 193611-05-1 ]
[ 141-90-2 ]
1-[2-t-butyl-6-trifluoromethylpyrimidin-4-yl]-4-[3-(4-hydroxypyrimidin-2-ylmercapto)propyl]hexahydro-1H-1,4-diazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; sodium iodide; In DMF (N,N-dimethyl-formamide); at 100℃; for 4h;	5 g 0.013 mol) of the product obtained in d) were dissolved in 25 ml of dimethylformamide and added dropwise to a stirred solution at 1000 C. of 2.03 g (0.016 mol) of 2-thiouracil, 0.38 g (0.016 mol) of lithium hydroxide and 1 g of sodium iodide in 50 ml of dimethylformamide over the course of 1 h. After reaction for 3 hours, the solvent was removed by distillation under reduced pressure, and the residue was mixed with 150 ml of water and extracted twice with ethyl acetate. The residue obtained after washing with water, drying with sodium sulfate and concentrating was purified by chromatography. (Flash chromatography, silica gel, mobile phase methylene chloride with 2.5-5% methanol). Yield: 4 g of pale oil NMR:CDCl3. delta 1.3(s,9H); 1.85-2.25(m,4H); 2.6(m,4H); 2.8(m,2H); 3.2(t,2H); 3.5(m,2H); 4.0(m,2H); 6.2(d,1H); 6.5(s,1H); 7.8(d;1H)

Reference： [1]Patent: US6352981,2002,B1 .Location in patent: Page column 15-16

65
[ 193611-13-1 ]
[ 141-90-2 ]
[ 193607-68-0 ]

Reference： [1]Patent: US6352981,2002,B1 .Location in patent: Page column 16-17

66
[ 147804-02-2 ]
[ 141-90-2 ]
4-hydroxy-2-[(4,4-difluoro-3-butenyl)-sulfanyl]-pyrimidine [ No CAS ]

Reference： [1]Patent: WO2004/26858,2004,A1 .Location in patent: Page/Page column 69-70

67
[ 36209-51-5 ]
C₂₃H₁₉BrNO₂Pol [ No CAS ]
[ 872-35-5 ]
[ 3004-42-0 ]
[ 52431-78-4 ]
[ 141-90-2 ]
[ 86-93-1 ]
[ 15264-63-8 ]
C₂₆H₂₂N₃O₂PolS [ No CAS ]
C₂₇H₂₂N₃O₃PolS [ No CAS ]
C₃₀H₂₄N₅O₂PolS [ No CAS ]
C₃₀H₂₃N₄O₃PolS [ No CAS ]
C₃₁H₂₄N₃O₃PolS [ No CAS ]
C₃₀H₂₅N₆O₂PolS [ No CAS ]
C₃₀H₂₄N₅O₃PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 20h;Combinatorial reaction / High throughput screening (HTS);	Each resin from Step 3 (50 mg each, 50 mumol) was distributed into 32 fritted syringes (Torvig, 50 mg each, 50), for a total of 64 syringes, and was swelled in NMP (1 mL) for 30 min. The solvent was removed from each syringe by filtration. Solutions of each of the sixteen building blocks listed below (10 mmol each) and DIEA (3.5 mL, 20 mmol) in NMP (10 mL) were prepared. 3 mL of solutions C1-C8 were added to the syringes containing the product incorporating building block A1, and 3 mL of solutions C9-C16 were added to the syringes containing the product incorporating building bock A2. The suspensions were then shaken for 20 h on a Titer Plate Shaker. The reaction mixtures were each filtered and washed 5 times with methylene chloride (5 mL), 3 times with THF (5 mL), three times with THF/H2O (3/1 v/v, 5 mL), and three times with THF (5 mL) and the resins were dried overnight under vacuum.

Reference： [1]Patent: US2006/167057,2006,A1 .Location in patent: Page/Page column 61-63

68
[ 638-45-9 ]
[ 141-90-2 ]
2-(hexylthio)pyrimidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran;	Step A: 2-Hexanethio-4-hydroxypyrimidine To a stirred suspension of 10 g of thiouracil in THF (100 mL) was added triethylamine (22 mL) and iodohexane (11.5 mL). The mixture was heated to and maintained at reflux for 3 h. The heating bath was removed and the mixture was stirred overnight. Iodohexane (2 mL) was added and the mixture was brought to and maintained at reflux for 8 h. The heating bath was removed and the mixture was stirred overnight. Iodohexane (2 mL) was added and the mixture was brought to and maintained at reflux for 3 h. The mixture was allowed to cool to room temperature and the THF was removed under reduced pressure. The residue was diluted with water and extracted 3* with ethyl acetate. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated. The product was recrystallized from hexanes giving 8.45 g of the title compound. 1H NMR (500 MHz, CDCl3): delta 7.78 (1H,d, J=7 Hz); 6.23 (1H, d, J=7 Hz); 3.20 (2H, t, J=7.5 Hz); 1.73 (2H, m); 1.44 (2H, m); 1.32 (4H, m); 0.90 (3H, t, J=7 Hz).
	With triethylamine; In tetrahydrofuran;	Step A 2-Hexanethio-4-hydroxypyrimidine To a stirred suspension of 10 g of thiouracil in THF (100 mL) was added triethylamine (22 mL) and iodohexane (11.5 mL). The mixture was heated to and maintained at reflux for 3 h. The heating bath was removed and the mixture was stirred overnight. Iodohexane (2 mL) was added and the mixture was brought to and maintained at reflux for 8 h. The heating bath was removed and the mixture was stirred overnight. Iodohexane (2 mL) was added and the mixture was brought to and maintained at reflux for 3 h. The mixture was allowed to cool to room temperature and the THF was removed under reduced pressure. The residue was diluted with water and extracted 3* with ethyl acetate. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated. The product was recrystallized from hexanes giving 8.45 g of the title compound. 1H NMR (500 MHz, CDCl3): delta 7.78 (1H, d, J=7 Hz); 6.23 (1H, d, J=7 Hz); 3.20 (2H, t, J=7.5 Hz); 1.73 (2H, (2H, m); 1.32 (4H, m); 0.90 (3H, t, J=7 Hz).

Reference： [1]Patent: US6498165,2002,B1
[2]Patent: US6329380,2001,B1

69
[ 876028-62-5 ]
[ 141-90-2 ]
2-{3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propylsulfanyl}-pyrimidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; potassium iodide; In N,N-dimethyl-formamide; at 20 - 50℃; for 21h;	EXAMPLE 3:; 2-(3-f4-(2-terf-Butvl-6-cvclobutvl-pyrimidin-4-yl)-piperazin-1-vll-propylsulfanvl)-pyrimidin-4-ol fumarate; 1.0 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidine (2.85 mmol), 0.38 g of 2-mercapto-pyrimidine-4-ol (2.97 mmol), 0.1 g of lithium hydroxide (4.18 mmol) and a spatula tip of potassium iodide were dissolved in 20 ml of dimethylformamide. The mixture was stirred at room temperature for 16 h and at 50C for 5 h. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel with dichloromethane/methanol (2-5 %). Fractions containing the product were combined and the solvent was evaported. The residue was dissolved in isopropanol. 144 mg of fumaric acid in isopropanol were added to precipitate the title compound as the fumarate salt. The precipitate was collected by filtration and dried to yield 0.3 g of the title product as a white solid.MS (ESI) m/z: 443.2 [M+H]+1H-NMR (DMSO): 8 [ppm] 11.2 (s, broad, 1H), 7.85 (d, 1H), 6.6 (s, 2H, fumarate), 6.4 (s, 1H), 6.1 (d, 1H), 3.6 (m, 4H), 3.4 (m, 1H), 3.15 (m, 2H), 2.4-2.6 (m, 6H), 2.1-2.3 (m, 4H), 1.8-2.0 (m,4H), 1.25 (s,9H).

Reference： [1]Patent: WO2006/15842,2006,A1 .Location in patent: Page/Page column 49-50

70
ethyl acetate n-hexane [ No CAS ]
[ 97582-36-0 ]
[ 141-90-2 ]
2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-4-hydroxypyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; potassium carbonate;tetrabutylammomium bromide; In ethyl acetate; butanone;	EXAMPLE 14 STR29 To a mixture of 0.30 g of 4-acetyl-3-hydroxy-2-propylbenzyl chloride, 0.20 g of <strong>[141-90-2]4-hydroxy-2-mercaptopyrimidine</strong>, 0.20 g of anhydrous potassium carbonate and 4 ml of methyl ethyl ketone was added a catalytic amount of tetra-n-butylammonium bromide. The mixture was stirred at 60 C. for 1 day. A 1N aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture to fractionate. The organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a mixture of hexane-ethyl acetate (1:2) gave 0.10 g of 2-[(4-acetyl-3- hydroxy-2-propylbenzyl)thio]-4-hydroxypyrimidine. Melting point: 177 C.

Reference： [1]Patent: US4803211,1989,A

71
[ 141-90-2 ]
[ 2001-93-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With diphosphorus pentasulfide; In pyridine; water;	Preparation of pyrimidine-2,4-dithiol [formula (VII)] for use in step (B) of the process A suspension of 2-thiouracil (32.0 g, 0.25 mole) in pyridine (150 ml) was stirred at room temperature and treated portionwise with phosphorus pentasulphide (21.25g) over 40 minutes. The reaction mixture was then refluxed for 45 minutes giving a homogeneous solution which was then cooled and treated with iced water (250 ml) and the resultant mixture stirred at 80 - 90C for 2 hours during which time hydrogen sulphide was evolved and a solid formed. The mixture was cooled and acidified with conc. hydrochloric acid and filtered. The solid was washed thoroughly with water and dried giving the dithiol as a yellow powder (28.6 g; 79%). The product was analyzed for sulphur content with the following results:

Reference： [1]Patent: EP294060,1988,A2

72
silver nitrate [ No CAS ]
[ 141-90-2 ]
2Ag⁽¹⁺⁾*C₄H₂N₂OS^(2-)={Ag₂C₄H₂N₂OS} [ No CAS ]

Reference： [1]Berichte der Deutschen Chemischen Gesellschaft,1914,vol. 47,p. 1377 - 1393

73
Pt⁽²⁺⁾*2NH₂C(CH₂OH)2CH₂O^(1-)*H₂O = Pt(NH₂C(CH₂OH)2CH₂O)2*H₂O [ No CAS ]
[ 141-90-2 ]
[ 93833-56-8 ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 2657 - 2660

74
[ 2273-45-2 ]
[ 141-90-2 ]
2(CH₃)2SnOH⁽¹⁺⁾*OSN₂C₄H₂^(2-)=((CH₃)2SnOH)2(ON₂SC₄H₂) [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1984,vol. 83,p. 79 - 86

75
[ 1067-55-6 ]
[ 141-90-2 ]
[ 90101-11-4 ]

Reference： [1]Inorganica Chimica Acta,1984,vol. 83,p. 79 - 86

76
Pt⁽²⁺⁾*2NH₂C(CH₃)2CH₂O^(1-)*2H₂O = Pt(NH₂C(CH₃)2CH₂O)2*2H₂O [ No CAS ]
[ 141-90-2 ]
[ 93833-57-9 ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 2657 - 2660

77
[ 10025-99-7 ]
[ 141-90-2 ]
[ 347894-62-6 ]

Reference： [1]Inorganica Chimica Acta,2001,vol. 315,p. 36 - 43

78
[ 21434-59-3 ]
[ 141-90-2 ]
(2-thiouracil)(ethionine)palladium(II) chloride [ No CAS ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1995,vol. 34,p. 878 - 882

79
[ 21434-62-8 ]
[ 141-90-2 ]
(2-thiouracil)(ethionine)platinum(II) chloride [ No CAS ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1995,vol. 34,p. 878 - 882

80
cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate [ No CAS ]
silver perchlorate [ No CAS ]
[ 141-90-2 ]
[(2,2'-bipyridine)2Ru(II)(μ-2-thiouracil dianion)Ru(II)(2,2'-bipyridine)2] perchlorate trihydrate [ No CAS ]

Reference： [1]Journal of the Chemical Society. Dalton Transactions (2001),2002,p. 2348 - 2353

81
bis(acetonitrile)bis(2,4-pentanedionato)ruthenium(II) [ No CAS ]
[ 141-90-2 ]
[Ru(III)2Ru(II)(O,O-acetylacetonate)3(μ-O,O,γ-C-acetylacetonate)3(μ3-S)] [ No CAS ]

Reference： [1]Inorganic Chemistry,2003,vol. 42,p. 1322 - 1327

82
(C₆H₅)2PCH₂P(C₆H₅)2*2Au⁽¹⁺⁾*2CF₃CO₂^(1-)=((C₆H₅)2PCH₂P(C₆H₅)2)Au₂(CF₃CO₂)2 [ No CAS ]
[ 141-90-2 ]
[ 596127-44-5 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 7778 - 7779

83
[ 141-90-2 ]
[ 302-72-7 ]
[ 7646-85-7 ]
[ 174843-26-6 ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1996,vol. 26,p. 305 - 320

84
[ 141-90-2 ]
[ 302-72-7 ]
[ 7646-79-9 ]
[ 174843-24-4 ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1996,vol. 26,p. 305 - 320

85
[ 141-90-2 ]
[ 302-72-7 ]
copper dichloride [ No CAS ]
[Cu₂(C₃H₆NO₂)(C₄H₃N₂OS)(OH)2]*2H₂O = Cu₂C₇H₁₁N₃O₅S*2H₂O [ No CAS ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1996,vol. 26,p. 305 - 320

86
[ 141-90-2 ]
[ 785-30-8 ]
N-(4-((Z)-(6-oxo-2-thioxo-1,2,3,4-tetrahydro-6l5-pyrimidin-5-yl)diazenyl)phenyl)-4-((E)-(6-oxo-2-thioxo-1,2,5,6-tetrahydropyrimidin-5-yl)diazenyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		0.1 mole of <strong>[785-30-8]4-amino-N-(4-aminophenyl)benzamide</strong> was mixed with HCl (0.2 mol in 25 mldistilled water) and diazotized below 50C withNaNO2(0.1mole) in distilled water (30ml). Theresulting diazonium chloride was coupled with analkaline solution of 2- thiouracil (0.1mole) below50C with equimolar ratio (0.02 mole). The reactionmixture was stirred under reflux for ?1hr. The volumeof the resultant solution was reduced to a half byevaporation then the solid product was precipitated,separated, washed with Et2O and dried in vacuumover calcium chloride (Scheme. 1) .

Reference： [1]Oriental Journal of Chemistry,2015,vol. 31,p. 1897 - 1913

87
[ 141-90-2 ]
[ 108229-82-9 ]
9-bromopyrimido[2,1:2,3]thiazolo[4,5-b]quinoxalin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In N,N-dimethyl-formamide; acetonitrile; for 16h;Reflux;	To a solution of compound 1 (2.78 g, 0.01 mol)in acetonitrile (50 mL), DMF (10 mL), anhydrouspotassium carbonate (2.0 g) and 2-thiouracil (1.54 g,0.012 mol) were added. The reaction mixture washeated under reflux for 16 h. After completion of the reaction, the reaction mixture was filtered to remove the potassium carbonate, then the solution was allowed to stand overnight at room temperature. The separated solid was filtered, dried and purified by column chromatography using an elution system chloroform : methanol (5 : 0.1, v/v) to give the product. Yield: 50%; (brown powder): m.p. 237-239 C;IR (KBr, cm -1 ): 1712 (C=O), 1594 (C=N). 1 H NMR(DMSO-d 6 , delta , ppm): 6.54 (d, 1H, J = 7 Hz, CH-C=O-pyrimidine), 8.02-8.08 (m, 3H, Ar-H),8.41 (d, 1H, J = 7 Hz, CH-N-pyrimidine). 13 C NMR(DMSO-d 6 , delta , ppm): 112.09 (CH-C=O-pyrimidine),123.19-138.74 (6Ar-C), 144.47, 146.33 (3C=N),151.25 (CH-N=C-pyrimidine), 159.60 (C=O). MS(m/z), 64 (M + - C 8 H 3 BrN 3 OS; 100%), 332 (M + ;69%), 333 (M + + 1; 12%), 334 (M + + 2; 67%).Analysis: calcd. for C 12 H 5 BrN 4 OS (333.16): C,43.26; H, 1.51; N, 16.82; S, 9.62%; found: C, 43.39;H, 1.43; N, 16.98; S, 9.84%.

Reference： [1]Acta poloniae pharmaceutica,2017,vol. 74,p. 445 - 458

88
[ 141-90-2 ]
[ 616-38-6 ]
[ 5751-20-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrabutylammomium bromide; potassium carbonate; at 120℃; for 8h;	Step 1. Preparation of 2-methylthio-4-pyrimidinone: 128 g of thiouracil, 500 g of dimethyl carbonate, 300 g of potassium carbonate, 1 g of tetrabutylammonium bromide, and heated to 120 for 8 hours, after the reaction, ,Cooled to room temperature, filtered, and the filtrate was decompressed to recover unreacted dimethyl carbonate. The residue was added to 300 ml of water and extracted with 300 ml of ethyl acetate and dried.Filtration, the filtrate was added to 100 ml of petroleum ether was recrystallized to give 132g of a white powder, yield 93%;
92.6%	With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 6h;	To a solution of thiouracil (13, 10 g, 78.1 mmol), tetrabutylammonium bromide (12.59 g, 39.1 mmol), and K2CO3 (16.2 g, 117 mmol) in dimethylformamide (DMF), dimethylcarbonate (30 mL) was slowly added dropwise when thetemperature was raised to 120 °C. After addition, the mixturewas stirred at 120 °C for 6 h. After filtering K2CO3, water was added to the filtrate which was then extracted with ethyl acetate. The organic phases were combined, dried over Na2SO4, and concentrated in vacuo. The residue was purified by passing the organic extract through a silica gel column using dichloromethane (DCM)/MeOH (75:1) to give the product14 as a white solid (10.27 g, 92.6percent); m.p. 204.4?205.3 °C.1H NMR (300 MHz, CDCl3) delta 7.88 (d, J = 6.5 Hz, 1H), 6.23(d, J = 6.6 Hz, 1H), 2.58 (s, 3H); 13C NMR (75 MHz, CDCl3)delta 164.7, 162.8, 155.0, 111.1, 13.4; HRMS ([M + H]+): m/zcalcd for C5H6N2OS: 143.0279; found: 143.02739.

Reference： [1]Patent: CN107488175,2017,A .Location in patent: Paragraph 0008; 0010
[2]Journal of Chemical Research,2019,vol. 43,p. 14 - 19

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H372	Causes damage to organs through prolonged or repeated exposure
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 141-90-2 ] {[proInfo.proName]}

Quality Control of [ 141-90-2 ]

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Calculated chemistry of [ 141-90-2 ]

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Medicinal Chemistry

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[ 141-90-2 ] Synthesis Path-Upstream 1~19

[ 141-90-2 ] Synthesis Path-Downstream 1~88

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Alcohols

Amides

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Pyrimidines

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[ 141-90-2 ]

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[ 141-90-2 ]