Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.Cl.[CH3:15][O:16][C:17]1[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=1>C(O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:22][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([S:12][CH3:13])[N:3]=2)[NH:20][N:21]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 4-chloro-2-(methylthio)-6-(trifluoromethyl)pyrimidine (2.29 g) in absolute ethanol (50 mL) was added DIEPA (4.4 mL) and 5-methoxy-1H-pyrazol-3-amine hydrogen chloride salt (1.46 g). The resulting solution was heated at 90° C. for over night. The solvent was evaporated under reduced pressure. The crude compound was purified by Gilson (10-60% MeCN/H2O, 15 minutes) to give N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine as solid (0.64 g). m/z 306. N-(3-methoxy-1H-pyrazol-5-yl)-2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-amine (240 mg) was dissolved in methylene chloride (5 mL), MCPBA (529 mg) was added. The resulting solution was stirred at room temperature for 0.5 hours and separate between methylene chloride and saturated sodium carbonate water solution. The organic layer was dried and solvent was removed under reduced pressure and low temperature. The crude product (270 mg) was carried on to do next step without further purification. m/z 338.
Workup
- customThe solvent was evaporated under reduced pressure
- customThe crude compound was purified by Gilson (10-60% MeCN/H2O, 15 minutes)
Sources & evidence
- ORD record
- ord-a3834143e34d4281a1cb9762b51be000
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088784B2
Linked notes
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