p-Toluenesulfonic acid → 2-(5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)-3-phenethyl-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4-amino-N-phenethyl-2-(trifluoromethyl)nicotinamide (25.5 mg, 0.082 mmol), 5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazole-4-carbaldehyde (17 mg, 0.082 mmol) and TsOH (1.4 mg, 0.008 mmol) in toluene was heated at reflux overnight. The reaction was then filtered and to the crude mixture was added manganese oxide. The reaction was heated at 110° C. for 4 h. The reaction mixture was filtered, concentrated and purified with silica gel chromatography providing a solid, 2-(5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)-3-phenethyl-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one (7 mg). 1H NMR (400 MHz, CDCl3) δ 9.02 (s, 1H), 8.76 (d, 1H), 7.69 (m, 1H), 7.51 (m, 1H), 7.48 (d, 1H), 7.32 (m, 5H), 4.20 (m, 2H), 3.32 (m, 2H), 2.07 (s, 6H). MS m/z 496.5 (M+H)+.

Provenance & Evidence