Sodium Methoxide → (6-Chloropyrimidin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

(6-Chloro-4-pyrimidinyl)methyl benzoate (Intermediate 24, 394 mg, 1.584 mmol) was dissolved in methanol (16 mL), cooled to 0° C. and treated with sodium methoxide (8.56 mg, 0.158 mmol). The resulting mixture was stirred for 4 hours. A further quantity of sodium methoxide (8.56 mg, 0.158 mmol) was added and the resulting mixture was stirrred for 18 hours. The reaction mixture was cooled to 0° C. and a further quantity of sodium methoxide (8.56 mg, 0.158 mmol) was added and the reaction mixture was stirred for 3 hours. The reaction mixture was evaporated under reduced pressure and the residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-100% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a white solid (132 mg);

Provenance & Evidence