Dimethylformamide dimethyl acetal → HCID 69230482, compound

Participants

Reaction Steps

Part A. A solution of methyl 4-acetylbenzoate (1.00 g, 5.61 mmol) and dimethylformamide dimethyl acetal (746 μL, 5.61 mmol) in ethanol (5 mL) is heated to reflux for 12 h. The solution is cooled and evaporated, and the residue is separated by column chromatography to afford the product as a mixture of methyl and ethyl esters of 4-(3-dimethylamino-acryloyl)benzoic acid (679 mg). A portion of this material (121 mg) is dissolved in ethanol (5 mL) and treated with 4-isopropyl-benzamidine (81 mg). The solution is heated to reflux for 12 h., cooled, filtered through celite, and evaporated. The residue is separated by column chromatography (silica gel, 1:4 ethyl acetate-hexane) to afford the product, ethyl 4-[2-(4-isopropyl-phenyl)-pyrimidin-4-yl]-benzoate.

Provenance & Evidence