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

Participants

Reaction Steps

To a solution of N-(3-aminobenzyl)-3-nitrobenzenesulfonamide hydrochloride (0.400 g, 1.16 mmol) and 2,4,5-trichloropyrimidine (0.12 mL, 1.06 mmol) in DMF (2.8 mL) was added potassium carbonate (0.51 g, 3.7 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with saturated (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 660 mg of crude residue, which was purified by Combi-Flash column chromatography (12 g column, 0 to 30% EtOAc in hexane) to give the desired product (135 mg, 28%). LCMS for C17H13Cl2N5O4S (M+H)+: m/z=453.9, 455.9, 457.9. 1H NMR (400 MHz, CD3OD): δ 8.85 (s, 1H), 8.48 (t, J=2.0 Hz, 1H), 8.29 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 8.21 (s, 1H), 8.08 (ddd, J=8.0, 1.6, 0.8 Hz, 1H), 7.64 (t, J=8.0 Hz, 1H), 7.41 (m, 2H), 7.17 (t, J=8.0 Hz, 1H), 4.21 (s, 2H).

Provenance & Evidence