Potassium Carbonate → N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}-3-nitrobenzamide

Participants

Reaction Steps

To a solution of N-(3-aminobenzyl)-3-nitrobenzamide hydrochloride (0.70 g, 2.3 mmol) and 2,4,5-trichloropyrimidine (0.237 mL, 2.07 mmol) in DMF (5.5 mL) was added potassium carbonate (1.0 g, 7.2 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc twice. The combined organics were washed with water, dried, filtered and concentrated to give 1.25 grams of crude material, which was triturated with MeOH/EtOAc to give the desired product as an off-white powder (665 mg, 77%). LCMS for C18H13Cl2N5O3 (M+H)+: m/z=418.0, 420.0, 422.0. 1H NMR (400 MHz, DMSO-d6): δ 9.53 (s, 1H), 9.49 (t, J=2.0 Hz, 1H), 8.74 (t, J=2.0 Hz, 1H), 8.36 (m, 3H), 7.78 (t, J=8.0 Hz, 1H), 7.52 (s, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.34 (t, J=7.6 Hz, 1H), 7.15 (d, J=8.0, 1H), 4.52 (d, J=6.0 Hz, 2H).

Provenance & Evidence