Sodium Carbonate → HCID 178432674, compound

Participants

Reaction Steps

A mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (80 mg, 0.33 mmol), methylboronic acid (Aldrich Chemical Company) (49 mg, 0.82 mmol), tris(dibenzylideneacetone) dipalladium(0) (Aldrich Chemical Company) (9.4 mg, 0.0103 mmol) and triphenylphosphine (Aldrich Chemical Company) (10.8 mg, 0.042 mmol) in a mixed solvent (1000 μL of toluene, 500 μL of 1.0 M Na2CO3, and 250 μL of ethanol) was heated at reflux under N2 overnight. Upon cooling to the room temperature, the reaction mixture was diluted with H2O (20 mL) and extracted with CHCl3 (4×40 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated with a rotary evaporator. This material was purified by preparative thin layer chromatography on silica gel with 1:1 THF:hexanes as eluant to afford 30 mg (62%) of the title compound as a yellow solid. 1H NMR (CDCl3; 400 MHz): δ 8.38 (s, 1), 7.74 (d, 2, J=7.0), 7.53 (t, 2, J=7.0), 7.45 (t, 1, J=7.0), 6.87 (d, 1, J=1.7), 2.79 (s, 3), 2.74 (s, 3). MS m/z: 224 (M+1), 222 (M−1).

Provenance & Evidence