Acetonitrile → 4-[(4-Chlorophenyl)sulfanyl]-6-ethyl-5-fluoropyrimidine

61.0 g of 4-chloro-6-ethyl-5-fluoropyrimidine was added to 600 ml of acetonitrile, and 60.4 g of 4-chlorothiophenol was added thereto followed by lowering the temperature to 10° C. 66.1 ml of diisopropylethylamine was added to the resulting solution, and reacted for 2 hours while maintaining the temperature at room temperature. 100 ml of dichloromethane and 300 ml of water were added to the resulting mixture to separate layer, and the resulting aqueous mixture was extracted with 300 ml of dichloromethane. The organic layer was dried over magnesium sulfate, concentrated under a reduced pressure, and crystallized at 5° C. in 305 ml of isopropanol and 122 ml of water to obtain the white title compound (85.6 g). Then, the filtrate was additionally concentrated under a reduced pressure, and crystallized at 5° C. in 30 ml of isopropanol to obtain 12.3 g of the title compound (total: 97.9 g, total yield: 96%).

1. additionwas added
2. customto 10° C
3. customreacted for 2 hours
4. customto separate layer
5. extractionthe resulting aqueous mixture was extracted with 300 ml of dichloromethane
6. dry with materialThe organic layer was dried over magnesium sulfate
7. concentrationconcentrated under a reduced pressure
8. customcrystallized at 5° C. in 305 ml of isopropanol

ORD record

ord-f3c7ae1f0c1046ed9c8766c3e07753c9

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263769B2