Pyridine → HCID 178515557, compound

Participants

Reaction Steps

To a stirred suspension of 8.42 g (70.2 mmol) of benzamidine and 8 mL (99.2 mmol) of pyridine in 150 mL of toluene was added dropwise over 10 min a solution of 7.68 g (46.1 mmol) of cinnamoyl chloride in 20 mL of toluene. The mixture was stirred for 10 min at room temperature and heated at reflux for 2 days. The mixture was cooled, diluted with 150 mL of ethyl acetate and extracted with two 125 mL portions of 5% aqueous HCl. The combined aqueous HCl extracts were neutralized by careful addition of 50% aqueous NaOH and extracted with two 250 mL portions of ethyl acetate. These ethyl acetate extracts were combined, dried over MgSO4 and rotovaped to afford 7.80 g of 5,6-dihydro-2,6-diphenylpyrimidin-4-one as a white solid.

Provenance & Evidence