2,4-Dichlorobenzoyl chloride → 2,4-dichloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide

Participants

Reaction Steps

6-Chloro-N4-(4-chlorophenyl)-pyrimidine-4,5-diamine I-(1A-1)a (34 g, 134 mmol) in pyridine (150 ml) was cooled to 0° C. and to it was added 2,4-dichlorobenzoyl chloride (25 ml, 178 mmol). The reaction was allowed to warm to ambient temperature overnight. The solid precipitate was collected by vacuum filtration and dried under high vacuum to yield the title compound I-(1A-1)b as a colorless solid (14 g, 25%). The pyridine solution was concentrated under reduced pressure and then triturated with methanol (500 ml) to provide additional material (35 g, 60%): +ESI MS (M+1) 427.4; 1H NMR: (400 MHz, DMSO-d6): δ 10.08 (s, 1H), 9.16 (s, 1H), 8.38 (s, 1H), 7.97 (d, J=8.7 Hz, 1H), 7.75 (d, J=2.0 Hz, 2H), 7.64–7.60 (m, 3H), 7.40 (d, J=8.7 Hz, 2H).

Provenance & Evidence