1-Propanol → 3-Pyrimidinecarboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromopyrimidine (1.59 g, 10 mmol), 1-propanol (1.5 mL, 20 mmol), bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.50 mmol) and tributylamine (3.72 g, 20 mmol) in DMF was stirred at 90° C. under a carbon monoxide balloon for 10 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with potassium dihydrogenphosphate (1.0 M, 20 mL, twice), water, and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was then purified by column chromatography (50:50:10 hexane-dichloromethane-ether) to give 3-pyrimidinecarboxylic acid methyl ester (715 mg, 52%).

Provenance & Evidence