Piperidine → 3-Phenylpropyl 4-(3,4-dichlorophenyl)-2-(2-furyl)-6-[(2-(4-methyl-1-piperazinyl)ethoxy)methyl]-1,4-dihydropyrimidine-5-carboxylate

Participants

Reaction Steps

A mixture of 3-phenylpropyl 4-(2-(4-methyl-1-piperazinyl)ethoxy)acetoacetate (500 mg, 1.38 mmol), 3,4-dichlorobenzaldehyde (241.5 mg, 1.38 mmol), 2-amidinofuran hydrochloride (202.3 mg, 1.38 mmol) and catalytic amounts of piperidine (1 μL) and acetic acid (10 μL) was stirred in N,N-dimethylformamide (5 mL) for 2 days at room temperature. Sodium hydrogen carbonate was added and the reaction mixture was stirred for an additional 5 days at room temperature before heating to 60° C. for 3 days. The DMF was removed in vacuo and ethyl acetate was added to the residue. The precipitate was removed by filtration and the filtrate was washed with water, sodium hydrogen carbonate solution and brine, dried and evaporated to yield an oil. The oil was further purified by flash chromatography to give the title compound (48 mg) as an oil. Electrospray MSm/z 611/613 [M+H]+.

Provenance & Evidence