Ammonium Hydroxide → 4-N-(5-bromo-2-nitrophenyl)pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-bromo-2-nitrophenyl)-2-chloropyrimidin-4-amine (6 g, 18.21 mmol) in 2-propanol (70 mL), in a pressure vessel, was carefully added ammonium hydroxide solution (150 mL) at RT. The reaction vessel was sealed and stirred at 90° C. (at 4.5 bar pressure) for 20 hr. The reaction mixture was cooled to 0° C. The resulting precipitate was collected by vacuum filtration, washed with water and dried in the vacuum oven to afford the title compound as an orange solid: 1H NMR (250 MHz, DMSO) δ 6.17 (1H, d, J=5.63 Hz), 6.34 (2H, br. s.), 7.39 (1H, dd, J=8.83, 1.98 Hz), 7.89-7.99 (2H, m), 8.34 (1H, d, J=2.13 Hz), 9.62 (1H, s); LC-MS: m/z+309.9, 311.7 (M+H)+.

Provenance & Evidence