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

Participants

Reaction Conditions

Reaction Steps

(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);

Provenance & Evidence