Sodium Carbonate → HCID 178432532, compound

Participants

Reaction Steps

A mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (230 mg, 0.94 mmol), 3-pyridinylboronic acid (Frontier Scientific) (139 mg, 1.13 mmol), tris(dibenzylideneacetone)dipalladium(0) (Aldrich Chemical Company) (22 mg, 0.024 mmol) and triphenylphosphine (Aldrich Chemical Company) (49 mg, 0.19 mmol) in a mixture of solvents (1.2 mL of toluene, 0.3 mL of 1.0 M Na2CO3 and 0.3 mL of ethanol) was heated at reflux under N2 for 40 h. Upon cooling to the room temperature, the reaction mixture was diluted with H2O (20 mL), and the crude product was extracted with CHCl3 (3×40 mL). The organic extracts were washed with H2O (50 mL), saturated NaCl (50 mL), dried over Na2SO4 and concentrated with a rotary evaporator. Chromatography on silica gel with a gradient eluant of MeOH (0-4%):CH2Cl2 (100-96%) afforded 171 mg (64%) of the title compound as a yellow solid. Mp: 252-254° C. 1H NMR (CDCl3; 400 MHz): δ 2.89 (s, 3), 6.99 (s, 1), 7.46 (m, 4), 7.78 (d, 2, J=7.1), 8.37 (d, 1, J=7.7), 8.66 (d, 1, J=3.9), 9.31 (s, 1), 9.50 (s, 1). MS m/z: 287 (M+1), 285 (M−1). HRMS: Calcd for M+H: 287.1297. Found: 287.1288.

Provenance & Evidence