Triphenylphosphine → HCID 178432640, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (200 mg, 0.82 mmol), 2-tributylstannylthiazole (Frontier Scientific) (338 mg, 0.90 mmol), tris(dibenzylideneacetone)dipalladium(0) (Aldrich Chemical Company) (19 mg, 0.021 mmol) and triphenylphosphine (Aldrich Chemical Company) (43 mg, 0.16 mmol) in anhydrous toluene (2 mL) was refluxed under N2 for 4 d. TLC showed that the reaction was not complete. Therefore, additional portions of 2-tributylstannylthiazole (338 mg, 0.90 mmol), tris(dibenzylideneacetone)dipalladium(0) (19 mg, 0.021 mmol) and triphenylphosphine (43 mg, 0.16 mmol) were added to the reaction mixture, and the mixture was stirred at 120° C. for 3 d. Upon cooling to the room temperature, the reaction was quenched with 5% HCl (50 mL) and the solution was extracted with CHCl3 (3×100 mL). The organic extracts were washed with H2O (2×150 mL), filtered through a pad of Celite, washed with saturated NaCl (150 ml), dried over Na2SO4 and concentrated with a rotary evaporator. Chromatography on silica gel with a gradient eluant of MeOH (1-3%):CH2Cl2 (99-97%) afforded 119 mg (50%) of the title compound as a yellow solid. Mp: 248-250° C. 1H NMR (acetone-d6; 400 MHz): δ 2.69 (s, 3), 7.01(s, 1), 7.57-7.47 (m, 3), 8.06 (d, 2, J=7.17), 8.97 (s, 1), 9.18 (s, 1), 10.76 (s, 1). MS m/z: 293 (M+1), 291 (M−1). HRMS: Calcd for M+H: 293.0861. Found: 293.0866.

Provenance & Evidence