Benzyl Alcohol → 2-Amino-4-benzyloxy-5-nitropyrimidine

Participants

Reaction Conditions

Reaction Steps

2-Amino-4-chloro-5-nitropyrimidine (0.70 g, 4.0 mmol) was added to a solution of sodium (0.12 g, 5.2 mmol) in benzyl alcohol (8 mL) under argon. The solution was heated in a 130° C. oil bath for 3 h, and approximately half of the benzyl alcohol was evaporated under reduced pressure. The residue was poured into water (50 mL) with constant stirring for 10 min. After neutralization with glacial acetic acid, a brown precipitate formed which was collected by filtration and washed with water. This solid was crystallized from benzene to give 5a as a golden crystalline solid: yield, 126 mg (13%); mp 164-167° C.; UV (pH 1) λmax 262 nm (ε=0.879×104), 295 (sh) (0.571×104); (pH 6.9) 235 (sh) (0.448×104), 273 (0.360×104), 326 (1.085×104); (pH 13) 273 (0.404×104), 327 (1.055×104); 1H NMR δ 5.51 (s, 2H, ArCH2), 7.35-7.54 (m, 5H, ArH), 8.05 (d, 2H, NH2, exchange with D2O), 8.92 (s, 1H, H-6); MS (EI) calcd. m/z for C11H10N4O3 246.0752, found 246.0758; Anal. (C11H10N4O3) C, H, N.

Provenance & Evidence