Ammonia → 4-Chloro-6-(2-chloro-5-methylanilino)pyrimidine

Participants

Reaction Conditions

Reaction Steps

Tetramethylene sulphone (10 ml) was added to 4,6-dichloropyrimidine (25.0 g, 170 mmol) and heated to 125° C. 2-Chloro-5-methylaniline (11.90 g, 84 mmol) was added portion wise over 20 mins. The reaction mixture was heated at 125° C. for 2 hours. The reaction was allowed to cool to room temperature and DCM (200 ml) was added. The mixture was basified to pH 9-10 with methanolic ammonia and evaporated onto silica (15 g). The residue was purified by column chromatography eluting with EtOAc:isohexane (10:90) to give a white solid (12.25 g, 29%). NMR (300 MHz): 2.3 (s, 3H), 6.7 (s, 1H), 7.0 (d, 1H), 7.4 (d, 1H), 7.5 (s, 1H), 8.4 (s, 1H), 9.4 (s, 1H); m/z 254 (MH+).

Provenance & Evidence