Tetrahydrofuran → Diethylether ethylacetate

Participants

Reaction Steps

Sodium hydride (previously washed in hexanes) was added to a solution of 2-(3-chloroanilino)-3-aminomethylpyridine (10.3 g, 44.1 mmole) in tetrahydrofuran (200 ml). The solution was stirred at room temperature for 5 minutes. 1,1'-Carbonyldiimidazole (10.7 g, 66.1 mmole) was added gradually to the solution with stirring; after the addition the solution was refluxed for 22 hours. The solvents were removed and H2O was added to the residue. The solid material was extracted in ethyl acetate, washed with H2O and dried over MgSO4. The MgSO4 was removed by filtration and the solvents by evaporation. The product was recrystallized out of ethyl acetate/ethyl ether yielding 5.7 g (21.9 mmole, 50% yield) of 1-(3-chlorophenyl)pyrido[2,3-d]pyrimidine-2(1H,3H)-one (mp 188°-187° C.), as a tan solid.

Provenance & Evidence