Potassium Carbonate → HCID 57961833, compound

Participants

Reaction Steps

To a solution of N-(3-aminophenyl)-3-nitrobenzenesulfonamide (1.00 g, 3.41 mmol) and 2,4,5-trichloropyrimidine (0.57 g, 3.1 mmol) in DMF (10 mL) was added potassium carbonate (0.52 g, 3.7 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 was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The crude was purified by combi-flash column chromatography to give the desired product (1.2 g, 88%). LCMS for C16H11Cl2N5O4S (M+H)+: m/z=439.9, 441.9. 1H NMR (400 MHz, DMSO-d6): δ 10.65 (s, 1H), 9.51 (s, 1H), 8.54 (t, J=2.1 Hz, 1H), 8.43 (ddd, J=8.2, 2.0, 1.0 Hz, 1H), 8.37 (s, 1H), 8.18 (ddd, J=8.0, 2.0, 1.0 Hz, 1H), 7.84 (t, J=8.0 Hz, 1H), 7.50 (t, J=2.0 Hz, 1H), 7.29 (ddd, J=8.2, 2.0, 1.2 Hz, 1H), 7.24 (m, 1H), 6.88 (ddd, J=8.0, 2.0, 1.2 Hz, 1H).

Provenance & Evidence