2,2,2-Trifluoroethanol → 2-Methylthio-4-(2,2,2-trifluoroethoxy)pyrimidine

2,2,2-Trifluoroethanol (3.74 g) was dissolved in N,N-dimethylformamide (50 mL), sodium hydride (about 60% in oil) (1.37 g) was added under ice-cooling, and the mixture was stirred at room temperature for 20 min. After ice-cooling again, 4-chloro-2-(methylthio)pyrimidine (5.0 g) was added, and the mixture was stirred at 0° C. for 1 hr. Saturated aqueous ammonia chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (5.1 g) as a slightly yellow oil.

1. temperaturecooling
2. temperatureAfter ice-cooling again
3. stirringthe mixture was stirred at 0° C. for 1 hr
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated under reduced pressure

ORD record

ord-9ce47e7d2d1247d6902f1a737bec97b1

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026370B2