Sodium Carbonate → HCID 178432605, 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-3-boronic acid (37 mg, 0.287 mmol), tris(dibenzylidene-acetone)dipalladium(0) (Aldrich Chemical Company) (4.7 mg, 0.0051 mmol, 0.025 eq) and triphenylphosphine (Aldrich Chemical Company) (10.8 mg, 0.041 mmol, 0.2 eq) in a mixed solvent (600 μL of toluene, 300 μL of 1.0 M Na2CO3, and 150 μL of ethanol) was heated at reflux under N2 for 17 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 a gradient eluant of EtOAc(0-25%):hexanes(100-75%) to afford 43.3 mg (73%) of an off-white solid. Mp: 232-233° C. 1H NMR (CDCl3; 400 MHz): δ 8.57 (s, 1), 8.04 (dd, 1, J=1.2, 2.9), 7.66 (m, 3), 7.59 (dd, 1, J=2.9, 5.0), 7.52 (t, 2, J=7.7), 7.46 (t, 1, J=7.7), 6.94 (d, 1, J=2.0), 2.86 (s, 3). MS m/z: 292 (M+1), 290 (M−1).

Provenance & Evidence