Diethyl Ether → 2-(2-Chloro-5-fluoropyrimidin-4-yl)propan-2-ol

Temperature

-78 °C

A stirred, −78° C. solution of 1-(2-chloro-5-fluoro-pyrimidin-4-yl)ethanone (10.06 g, 57.6 mmol) in tetrahydrofuran (100 mL) under nitrogen is reacted with a 3 M solution of methyl magnesium bromide in diethyl ether (124 mL, 72.04 mmol) and the resulting mixture is stirred at −78° C. for 20 minutes. The reaction is quenched with aqueous saturated ammonium chloride and the mixture is warmed to room temperature. The reaction mixture is extracted three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated under vacuum. The crude product is purified over silica gel with a 30 minute, 5% to 100% ethyl acetate in hexanes gradient, to give the title compound (7.06 g, 64%). ES/MS (m/e): (35C/37Cl) 191/193 (M+H).

1. customThe reaction is quenched with aqueous saturated ammonium chloride
2. temperaturethe mixture is warmed to room temperature
3. extractionThe reaction mixture is extracted three times with ethyl acetate
4. dry with materialThe combined organic layers are dried over sodium sulfate
5. concentrationconcentrated under vacuum
6. customThe crude product is purified over silica gel with a 30 minute

ORD record

ord-2a7797be6dd449df955cad82088e7e45

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629270B2