Ethyl Acetoacetate → Ethyl 6-methyl-4-(2-nitrophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-nitrobenzaldehyde (10 g, 66 mmol), thiazole-2-carboximidamide hydrochloride (10.8 g, 66 mmol), ethyl 3-oxobutanoate (8.6 g, 66 mmol) and sodium acetate (5.5 g, 66 mmol) in ethanol (250 mL) was stirred at 88° C. for 16 hours, then cooled to 25° C. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1) to give the title compound as a light yellow solid (12 g, 48%). The compound was characterized by the following spectroscopic data:

Provenance & Evidence