Acetic Acid → 2-Amino-4-benzyloxy-6-methyl-5-nitropyrimidine

Participants

Reaction Conditions

Reaction Steps

2-Amino-4-chloro-6-methyl-5-nitropyrimidine (Boon et al., J. Chem. Soc., 96-102 (1951)) (1.24 g, 6.58 mmol) was added to a solution of sodium (0.21 g, 9.13 mmol) in benzyl alcohol (14 mL) under argon. The solution was heated in a 135° C. oil bath for 3.5 h, and was poured into water (70 mL) with constant stirring for 10 min. After neutralization with glacial acetic acid, a yellow precipitate formed which was collected by filtration and washed with water. This solid was crystallized from benzene to give 5b as a bright yellow crystalline solid: yield, 0.57 g (33%); mp 159-160° C.; UV (pH 1) λmax 268 nm (ε=0.783×104), 345 (sh) (0.104×104); (pH 6.9) 282 (0.564×104),345(sh) (0.338×104); (pH 13) 282 (0.549×104), 345 (sh) (0.332×104); 1H NMR δ 2.35 (s, 3H, CH3), 5.44 (s, 2H, ArCH2), 7.34-7.46 (m,5H, ArH), 7.64(b s, 2H, NH2, exchange with D2O); MS (EI) calcd. m/z for C12H12N4O3 260.0908, found 260.0913; Anal. (C12H12N4O3) C, H, N.

Provenance & Evidence