4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine → 4-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Participants

Reaction Steps

To a solution of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (16.5 g, 58.90 mmol) in acetic acid (55 mL) was added methyl 2,2,2-trichloroethanecarboximidate (11 g, 62.35 mmol) dropwise with stirring. The reaction mixture was stirred at room temperature for 3 hr and then at 45° C. overnight. The resulting solution was diluted with 100 mL of water and the precipitate was collected by filtration. The solid was dried in a vacuum oven to give 19.5 g (81%) of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a light brown solid: 1H NMR (300 MHz, DMSO) delta 8.58 (d, J=4.8 Hz, 1H), 7.68 (t, J=4.5 Hz, 1H), 7.61-7.58 (m, 2H), 7.21 (s, 2H), 7.01 (d, J=5.1 Hz, 3H); LC-MS: m/z=+408 (M+H)+.

Provenance & Evidence