Sodium borohydride → 2-(4-Chloro-6-phenylpyrimidin-5-yl)ethanol

Participants

Reaction Steps

To a stirred solution of 2-(4-chloro-6-phenylpyrimidin-5-yl)acetaldehyde (450 mg) in dry methanol (10 mL), sodium borohydride (110 mg) was slowly added under nitrogen atmosphere at 0° C. The reaction mixture was stirred at room temperature for 2 hours and solvents were removed under reduced pressure. The resulting oil was diluted with dichloromethane (50 mL), washed with 10% NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to give a residue which was purified by column chromatography using MeOH/CHCl3 (0.2:9.8) as eluent to afford 2-(4-chloro-6-phenylpyrimidin-5-yl)ethanol (340 mg) as colorless oily liquid. 1H NMR (DMSO-d6): δ 2.89-2.94 (t, 2H), 3.53-3.58 (t, 2H), 4.81-4.85 (t, 1H), 7.50-7.61 (m, 5H), 8.92 (s, 1H).

Provenance & Evidence