Dimethylformamide → 1-(2-aminopyrimidin-4-yl)-6-bromo-2,3-dihydro-1H-1,3-benzodiazol-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (400 mg, 1.43 mmol) in DMF (4 mL) was added N,N′-carbonyldiimidazole (255 mg, 1.57 mmol). The reaction was stirred at 80° C. overnight. Another portion of N,N′-carbonyldiimidazole (69 mg, 0.43 mmol) was added and heating was continued for another 2 hr at 80° C. The reaction mixture was concentrated in vacuo, diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). The organics were dried over Na2SO4, filtered and concentrated in vacuo. The resulting yellow solid was slurried in ethyl acetate and filtered off to give the title compound as a yellow solid: 1H (500 MHz, DMSO) δ 6.93 (2H, br. s.), 7.00 (1H, d, J=8.35 Hz), 7.31 (1H, d, J=10.25 Hz), 7.45 (1H, d, J=5.67 Hz), 8.25 (1H, d, J=5.52 Hz), 8.58 (1H, s); LC-MS: m/z=+306.0, 307.9 (M+H)+.

Provenance & Evidence