Benzenesulfonamide, 3-amino- → 3-(5-Pyrimidinylamino)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-aminobenzenesulfonamide (110mg, 0.64 mmol), 5-bromopyrimidine (102 mg, 0.64 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.6 mg, 0.05 mmol), diacetoxypalladium (5.74 mg, 0.03 mmol) and cesium carbonate (250 mg, 0.77 mmol) in degassed DMA (1.9 mL) was heated **_in the microwave_** for 35 min at 130°C. LC MS FLA-04665-12-01 (pH extract 6-7) showed some product. Reaction was stopped. Extraction with AE + ethanol / aq. sat NH4Cl (pH7), then back extraction with DCM.The organics were dried over MgSO4 and concentrated _in vacuo._ The crude product was adsorbed on silica gel 40-60µm and purified by flash chromatography on silica gel 15-40µm eluting with 3.5 % of ethanol in dichloromethane (NH3 0.5 %) to provide 3-(pyrimidin-5-ylamino)benzenesulfonamide (30.0 mg, 18.77 %) as a yellow solid. 1H NMR,LC MS: FLA-04665-12-02a: OK

Provenance & Evidence