2-(PhenylaMino)pyriMidine-4-carbaldehyde synthesis

Yield:797793-40-9 78%

Reaction Conditions:

Stage #1: 2-anilino-4-(dimethoxymethyl)pyrimidinewith hydrogenchloride in water at 50; for 18 h;
Stage #2: with sodium carbonate in water; pH=9;

Steps:

3 Method 3; 2-ANILINOPYRIMIDIN-4-CARBALDEHYDE

A mixture OF 2-ANILINO-4-(DIMETHOXYMETHYL) PYRIMIDINE (Method 2; 26. 5g, 0. 108MOL) and 3M hydrochloric acid (108ML, 0. 324MOL) 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 x 100 ml). The combined extracts were washed with water (2 x 100 ml), dried (NA2SO4) and evaporated to give the title compound (16.2g, 78 %) as a brown solid. NMR: (CDC13) : 7.10 (t, 1H), 7.20 (d, 1H), 7.40 (t, 3H), 7.68 (d, 2H), 8.64 (d, 1H), 9.90 (s, 1H), m/z 232 [MH+MeOH] +.

References:

WO2004/101564,2004,A1 Location in patent:Page 33