(Diethylamino)sulfur trifluoride → 4-Chloro-6-(fluoromethyl)pyrimidine

Temperature

-78 °C

(Diethylamino)sulphur trifluoride (0.145 mL, 1.096 mmol) was added to DCM (5.5 mL), cooled to −78° C. and treated dropwise with a solution of (6-chloro-4-pyrimidinyl)methanol (Intermediate 25, 132 mg, 0.913 mmol) in DCM (2 mL) under argon. The resulting mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction was quenched by adding water (5 mL) and extracted with DCM (×2). The DCM layers were separated, combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-25% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil (40 mg);

1. temperatureto warm to room temperature
2. customThe reaction was quenched
3. additionby adding water (5 mL)
4. extractionextracted with DCM (×2)
5. customThe DCM layers were separated
6. customdried under magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by column chromatography (Biotage SP4)
9. washeluting with a gradient of 0-25% ethyl acetate and iso-hexane
10. additionProduct containing fractions
11. customevaporated under reduced pressure

ORD record

ord-794672e6e3da4a4998a7079b9b9785dc

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2