Sodium Carbonate → HCID 178432587, compound

Participants

Reaction Steps

A mixture of 4-chloro-2-methyl-6-phenylpyrrolo-[3,2-d]pyrimidine (Example 1(e)) (50 mg, 0.21 mmol), thiophene-2-boronic acid (37 mg, 0.287 mmol), tris(dibenzylidene-acetone)dipalladium(0) (Aldrich Chemical Company) (4.7 mg, 0.0051 mmol) and triphenylphosphine (Aldrich Chemical Company) (10.8 mg, 0.041 mmol) in a mixed solvent (600 μL of toluene, 300 μL, 1.0 M Na2CO3 and 150 μL of ethanol) was heated at reflux under N2 for 36 h. Upon cooling to the room temperature, the reaction mixture was diluted with H2O (20 mL) and extracted with CHCl3 (3×20 mL). The organic phase was dried over Na2SO4, filtered, and concentrated with a rotary evaporator. The crude material was purified by flash chromatography on silica gel with a gradient eluant of EtOAc(0-25%):hexanes(100-75%) to afford 37.2 mg (62%) of the title compound as a yellow solid. Mp: 178-179° C. 1H NMR (Acetone-d6; 400 MHz): δ 10.61 (s, 1), 8.21 (d, 1, J=4.5), 8.00 (d, 2, J=7.3), 7.73 (d, 2, J=4.5), 7.54 (t, 2, J=7.3), 7.48 (t, 1, J=7.3) 7.28 (t, 1, J=4.5), 6.96 (s, 1), 2.68 (s, 3). MS m/z: 292 (M+1), 290 (M−1). HRMS (NBA-NaI) m/z Calcd for M+H, C17H13N3S: 292.0908. Found: 292.0900.

Provenance & Evidence