Hydrochloric Acid → 2-Anilinopyrimidine-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-anilino-4-(dimethoxymethyl)pyrimidine (Method 2; 26.5 g, 0.108 mol) and 3M hydrochloric acid (108 ml, 0.324 mol) was stirred and heated at 50° C. for 18 hours. The reaction mixture was allowed to cool and the pH of the solution adjusted to 9 by careful addition of solid sodium carbonate. The mixture was extracted with EtOAc (5×100 ml). The combined extracts were washed with water (2×100 ml), dried (Na2SO4) and evaporated to give the title compound (16.2 g, 78%) as a brown solid. NMR: (CDCl3): 7.10 (t, 1H), 7.20 (d, 1H), 7.40 (t, 3H), 7.68 (d, 21), 8.64 (d, 1H), 9.90 (s, 1H), m/z 232 [MH+MeOH]+.

Provenance & Evidence