Benzyl Alcohol → 6-(Benzyloxy)-5-bromopyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

2,4-Diamino-5-bromo-6-chloropyrimidine (Phillips et. al., J. Org. Chem., 29, 1488-1490 (1963)) (2.3 g, 10 mmol) was added to a solution of sodium (0.29 g, 12.5 mmol) in benzyl alcohol (10 mL) under argon. The solution was heated in a 130° C. oil bath for 3 h and the benzyl alcohol was evaporated under reduced pressure to give a white solid. This solid was washed with water, and air dried. Crystallization from 50% aqueous ethanol gave white crystalline needles of 3f: yield, 2.32 g (76%); mp 165-166° C. (lit. 136° C.; Kosary et. al., Acta Pharm. Hung., 49, 241-247 (1989)); UV (pH 1) λmax 236 nm (ε=0.873×104), 291 (1.388×104); (pH 6.9) 236 (0.850×104), 277 (0.835×104); (pH 13) 234 (0.869×104), 277 (0.835×104); 1H NMR δ 5.30 (s, 2H, ArCH2), 6.15 (s, 2H, NH2, exchange with D2O), 6.32 (s, 2H, NH2, exchange with D2O), 7.31-7.45 (m, 5H, ArH); MS (EI) calcd. m/z for C11H11N4O79Br 294.0115, found 294.0127; calcd. m/z for C11H11N4O81Br 296.0094, found 296.0083; Anal. (C11H11N4OBr) C, H, N.

Provenance & Evidence