Benzene → 4-Amino-6-benzyloxy-5-nitropyrimidine

Participants

Reaction Conditions

Reaction Steps

4-Amino-6-chloro-5-nitropyrimidine (Boon et al., J. Chem. Soc., 96-102 (1951)) (1.5 g, 8.6 mmol) was added to a solution of sodium (0.23 g, 9.9 mmol) in benzyl alcohol (14 mL). The solution was heated in a 130° C. oil bath for 3.5 h, and was poured into benzene (50 mL). A yellow solid was collected by filtration and washed with benzene. Crystallization from benzene/ether afforded an analytically pure sample of 3a: yield, 0.71 g (34%); mp 149°-150° C.; UV (pH 1) λmax 284 nm (ε=0.368×104), 333 (0.488×104); (pH 6.9) 284 (0.329×104), 336 (0.470×104); (pH 13) 290 (0.344×104), 333 (0.494×104); 1H NMR δ5.50 (s, 2H, ArCH2), 7.33-7.49 (m, 5H, ArH), 8.12-8.24 (br d, 2H, NHa and NHb, exchange with D2O), 8.24 (s, 1H, H-2); MS (EI) calcd. m/z for C11H10N4O3 246.0752, found 246.0751; Anal. (C11H10N4O3) C, H, N.

Provenance & Evidence