7464-11-1|5,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidine| Ambeed

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Quality Control of [ 7464-11-1 ] Purity: 95% SDS Specification

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Product Details of [ 7464-11-1 ]

CAS No. :	7464-11-1
Formula :	C₆H₃Cl₂N₃S
M.W :	220.08
SMILES Code :	CC1=NC2=C(Cl)N=C(Cl)N=C2S1
MDL No. :	MFCD12828095
InChI Key :	ZXOQUXADNLREKJ-UHFFFAOYSA-N
Pubchem ID :	345639

Safety of [ 7464-11-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 7464-11-1 ]

* 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.

Downstream synthetic route of [ 7464-11-1 ]

[ 7464-11-1 ] Synthesis Path-Downstream 1~35

1
[ 5021-52-3 ]
[ 7464-11-1 ]

Yield	Reaction Conditions	Operation in experiment
54%	With N,N-dimethyl-aniline; trichlorophosphate; at 130℃; for 4.0h;	To a mixture of 2-methyl-4H-thiazolo[5,4-rf]pyrimidine-5,7-dione (7.5 g, 0.041 mol) in N^V-dimethylaniline (3.7 mL, 0.029 mol) was added phosphorous oxychloride (38.0 mL, 0.410 mol) and the mixture heated at 130 C for 4 h. The resulting black solution was cooled to RT, then carefully quenched with crushed ice and H2O, before being extracted with EtOAc. The organic layer was isolated, dried (MgSO4) and concentrated in vacuo to give a yellow solid. The solid was dissolved in DCM, then washed with an aqueous solution OfNaHCO3 <n="47"/>followed by brine, dried (Na2SO4) and concentrated in vacuo to give the title compound as a pale yellow solid (4.90 g, 54 %).1H NMR (300 MHz, CDCl3): delta 2.95 (s, 3 H).

References: [1]Patent: WO2008/152390,2008,A1 .Location in patent: Page/Page column 34; 45-46.
[2]Journal of the American Chemical Society,1951,vol. 73,p. 3862.

2
[ 7464-11-1 ]
[ 89712-91-4 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 3862.

3
[ 110-91-8 ]
[ 7464-11-1 ]
[ 1093074-92-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	In methanol; at 0℃; for 0.5h;	To a solution of 5,7-dichloro-2-methyl-thiazolo[5,4-c(]pyrimidine (4.1 g, 18.72 mmol) in MeOH (100 mL) was added morpholine (3.26 mL, 37.44 mmol) at 0 C and the mixture stirred at 0 C for 30 minutes. The resultant precipitate was collected by filtration and dried in vacuo at 40 0C to give the title compound as a cream solid (4.42 g, 89 %). 1H NMR (300 MHz, CDCl3): delta 2.74 (s, 3 H), 3.80-3.86 (m, 4 H) and 4.35 (m, 4 H).

References: [1]Patent: WO2008/152390,2008,A1 .Location in patent: Page/Page column 34; 46.

4
[ 31785-16-7 ]
[ 503-38-8 ]
[ 7464-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 0 - 130℃;	Intermediate 16; 5,7-Dichloro-2-methviri,31thiazolor5,4-<i1pyrimidineTo a stirred solution from 5-amino-2-methyl-l,3-thiazole-4-carbonitrile (Intermediate 15) in MeCN (3 mL) was added diphosgene drop-wise at O0C. The solution was stirred at 13O0C for 1 hour. The volatiles were evaporated under reduced pressure and purification by column chromatography afforded the title product. LCMS: 220 [M+H]+. 1U NMR (400 MHz, CDCl3) delta: 2.93 (s, 3H).

References: [1]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 73.

5
[ 7464-11-1 ]
[ 79578-98-6 ]
[ 1220517-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethanol; at 70℃; for 1.0h;	Intermediate 13; 5-Chloro-2-methyl-N-(l-methyl-lH-imidazol-4-yl)?,31thiazolor5,4-?pyrimidin-7-amineA mixture of 5,7-dichloro-2-methyl[l,3]thiazolo[5,4-d]pyrimidine (Intermediate 16, 380 mg, 1.73 mmol), DIPEA (0.754 mL, 4.32 mmol) and 1 -methyl- lH-imidazol-4-amine (prepared from Intermediate 1 as described in the synthesis of Intermediate 10, 201 mg, 2.07 mmol) in EtOH (15 mL) was heated for 1 hour at 700C, LCMS analysis indicated the reaction was complete. The 103496-1Ptitle product (400 mg) was obtained after filtration and was used in a subsequent step without any further purification.LCMS: 281 [M+H]+.1H NMR (300 MHz, DMSO-J6) delta ppm 10.29 (s, 1 H), 7.50 (d, J=I.32 Hz, 1 H), 7.37 (d, J=I.51Hz, 1 H), 3.70 (s, 3 H), 2.83 (s, 3 H).

References: [1]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 71-72.

6
[ 7464-11-1 ]
[ 1228947-14-5 ]
C₁₆H₂₁ClN₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		Into a 250 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed LiHDMS (10 mL, 1.00 equiv), 4-(morpholin-4-yl) cyclohexan-1-ol (1.86 g, 10.04 mmol, 1.00 equiv), and tetrahydrofuran (60 mL). The above mixture was stirred for 1 hour. Intermediate 45.3 (2.2 g, 10.00 mmol, 1.00 equiv) was added. The reaction was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum and crude purified using flash column chromatography to furnish 1.6 g (43%) of intermediate 55.1 as a dark green solid.

References: [1]Patent: WO2015/48281,2015,A1 .Location in patent: Paragraph 00516; 00517.

7
[ 558442-97-0 ]
[ 7464-11-1 ]
C₁₆H₂₂ClN₅OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium phosphate; In acetonitrile; at 85℃;	Into a 2000-mL 3-necked round-bottom flask, was placed a solution of compound 23.1 (50 g, 227.19 mmol, 1.00 equiv) in MeCN (1500 mL), K3P04 (145.2 g, 684.03 mmol, 3.01 equiv), and (lr,4r)-4-(morpholin-4-yl)cyclohexan-1-amine (50.4 g, 273.50 mmol, 1.20 equiv). The resulting solution was stirred overnight at 85 C in an oil bath. The reaction mixture was cooled to room remperature, solids were filtered out and the resulting mixture was concentrated under vacuum. The crude product was re-crystallized to furnish 56 g (67%) of intermediate 23.2 as a yellow solid.

References: [1]Patent: WO2015/48281,2015,A1 .Location in patent: Paragraph 00396; 00397.

8
[ 7464-11-1 ]
C₁₃H₂₄N₂O [ No CAS ]
C₁₉H₂₆ClN₅OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium phosphate; In acetonitrile; at 85℃;	A 50-mL round-bottom flask, was charged with a solution of intermediate 41.2 (111 mg, 0.49 mmol, 1.00 equiv) in CH3CN(10 mL), K3P04 (322 mg, 1.52 mmol, 3.07 equiv), and compound 23.1 (125 mg, 0.57 mmol, 1.15 equiv). The reaction was stirred overnight at 85 C in an oil bath. Solids were filtered out and solution was concentrated under vacuum. The crude product obtained was purified using flash column chromatography to yield 180 mg (89%) of intermediate 41.3 as a yellow solid.

References: [1]Patent: WO2015/48281,2015,A1 .Location in patent: Paragraph 00456; 00458.

9
[ 7464-11-1 ]
C₁₁H₂₂N₂O [ No CAS ]
C₁₇H₂₄ClN₅OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
160 mg	With N-ethyl-N,N-diisopropylamine; In iso-butanol; at 100℃; for 4.0h;Inert atmosphere;	To interemdiate 17.6 (123 mg, 0.62 mmol, 1.03 equiv) and compound 23.1 (132 mg, 0.60 mmol, 1.00 equiv) in 2-butanol (5 mL) was added DIEA (155 mg, 1.20 mmol, 2.00 equiv) and the resulting solution was stirred for 4 h at 100 C under nitrogen. The resulting mixture was concentrated under vacuum and crude was purified using flash column chromatography to furnish 160 mg of intermediate 29.1 as a white solid. LCMS (ES, m/z): 382 and 384 [M+H].

References: [1]Patent: WO2015/48281,2015,A1 .Location in patent: Paragraph 00417; 00418.

10
[ 7464-11-1 ]
trans-4-[6-azaspiro[2.5]octan-6-yl]cyclohexan-1-amine [ No CAS ]
C₁₉H₂₆ClN₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
140 mg	With potassium phosphate; In acetonitrile; at 80℃;	Into a 50 mL round-bottom flask, was placed a solution of intermediate 38.2 (121 mg, 0.58 mmol, 1.05 equiv) in CH3CN (10 mL),compound 23.1 (121 mg, 0.55 mmol, 1.00 equiv) and K3P04 (352 mg, 1.66 mmol, 3.00 equiv). The reaction was stirred overnight at 80 C. The solids were filtered out and the resulting solution was concentrated under vacuum. The crude was purified using flash column chromatography to give 140 mg (65%) of intermediate 38.3 as a white solid.

References: [1]Patent: WO2015/48281,2015,A1 .Location in patent: Paragraph 00445; 00447.

11
[ 7464-11-1 ]
2-methyl-N₅-(1-methyl-1H-pyrazol-4-yl)-N₇-((1r,4r)-4-morpholinocyclohexyl)thiazolo [5,4-d]pyrimidine-5,7-diamine [ No CAS ]