Acetic Acid → 3-(2-Thienyl)propyl 2-(2-furyl)-4-(4-methyl-3-nitrophenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-1,4-dihydropyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-thienyl)propyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate (4.0 g, 11.32 mmol), 4-methyl-3-nitrobenzaldehyde (1.87 g, 11.32 mmol), 2-amidinofuran hydrochloride (1.65 g, 11.32 mmol), morpholine (1.48 ml, 16.98 mmol), acetic acid (1.29 ml, 22.64 mmol), and sodium sulfate (3.21 g, 22.64 mmol) was stirred in ethanol (45 ml) for 1 hour at room temperature and then heated to 40° C. for 9 days. The ethanol was removed in vacuo and ethyl acetate was added to the residue. 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 and RP-HPLC to give the title compound (120 mg) as an oil. Electrospray MS m/z 593 [M+H]+, m/z 297 [M+2H]++.

Provenance & Evidence