Benzyl Alcohol → 6-Benzyloxy-5-nitro-pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

2,4-Diamino-6-chloro-5-nitropyrimidine (O'Brien et. al., J. Med. Chem., 9, 573-575 (1966)) (1.0 g, 5.28 mmol) was added to a solution of sodium (0.14 g, 6.08 mmol) in benzyl alcohol (9 mL). The solution was heated in a 160° C. oil bath for 3.5 h and the solvent was evaporated under reduced pressure to provide a yellow solid. This solid was washed with water, and air dried. Crystallization from benzene/ether gave a pale yellow filamentous solid: yield, 0.69 g (50%); mp 194°-195° C. (171° C.; Kosary et. al., Acta. Pharm. Hung., 49, 241-247 (1989)); UV (pH 1) λmax 236 nm (sh) (ε=1.452×104), 264 (0.522×104), 321 (1.294×104); (pH 6.9) 242 (sh) (0.965×104), 337 (1.493×104); (pH 13) 242 (sh) (0.952×104), 338 (1.479×104); 1H NMR δ5.43 (s, 2H, ArCH2), 7.26 (br s, 2H, NH2, exchange with D2O), 7.33-7.51 (m, 5H, ArH), 7.93 (br s, 2H, NH2, exchange with D2O); MS (EI) calcd. m/z for C11H11N5O3 261.0861, found 261.0866; Anal. (C11H11N5O3).

Provenance & Evidence