Benzyl Alcohol → 4-(Benzyloxy)-2-chloro-5-nitropyrimidine

Participants

Reaction Conditions

Reaction Steps

Benzyl alcohol (5.57 g) was added to a suspension of sodium hydride (oil, 60%, 2.06 g) in DMF (100 mL) by small portions at 0° C., and the obtained mixture was stirred at 0° C. for 30 min. The reaction mixture was cooled to 0° C., 2,4-dichloro-5-nitropyrimidine (10.0 g) was added thereto, and the obtained mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (670 mg). 1H NMR (300 MHz, DMSO-d6) δ 5.62 (2H, s), 7.24-7.73 (5H, m), 9.28 (1H, s).

Provenance & Evidence