Acetic Acid → (2-Chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methanol

Participants

Reaction Steps

Methyl 2-chloro-6-(1-ethoxyvinyl)pyrimidine-4-carboxylate (3.5 g, 14.4 mmol) was dissolved in MeOH (35 mL), DMF (24.50 mL) and water (3.5 mL) by careful heating. The mixture was cooled on an ice-bath and sodium borohydride (1.47 g, 38.9 mmol) was added in small portions (about 50 mg every 5 min) keeping the temperature below 5° C. After 3.5 h acetic acid (3.96 mL, 69.23 mmol) was added. MeOH was evaporated and water was added. The mixture was extracted with diisopropyl ether (3×50 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The product was purified by column chromatography on silica eluting with a gradient of EtOAc in heptane to give the title compound as a solid 1.8 g (58%).

Provenance & Evidence