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

Temperature

0 °C

(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);

1. waitthe resulting mixture was stirrred for 18 hours
2. temperatureThe reaction mixture was cooled to 0° C.
3. stirringthe reaction mixture was stirred for 3 hours
4. customThe reaction mixture was evaporated under reduced pressure
5. customthe residue was purified by column chromatography (Biotage SP4)
6. washeluting with a gradient of 0-100% ethyl acetate and iso-hexane
7. additionProduct containing fractions
8. customevaporated under reduced pressure

ORD record

ord-28f2f809d8b848dfa79f7c0d0116d22a

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2