3,4-Dichlorobenzaldehyde → 3-Phenylpropyl 4-(3,4-dichlorophenyl)-6-[(2-(N,N-diethylamino)ethoxy)methyl]-2-methylthio-1,4-dihydropyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-phenylpropyl 4-(2-(N,N-diethylamino)ethoxy)acetoacetate (2.0 g, 5.96 mmol), 3,4-dichlorobenzaldehyde (1.15 g, 6.56 mmol), 2-methyl-2-thiopseudourea sulfate (0.913 g, 3.28 mmol) and sodium acetate (0.27 g, 3.28 mmol) was stirred in N,N-dimethylformamide (10 mL) for 24 hours at room temperature, then heated to 60° C. for 5 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. This oil was further purified by flash chromatography and RP-HPLC to give the title compound (114 mg) as an oil. The oil can be converted into a mono or dihydrochloride salt, by dissolution in ether and addition of one or two equivalents of hydrogen chloride. Electrospray MSm /z 564/566 [M+H]+.

Provenance & Evidence