Sodium Iodide → HCID 59553886, compound

Participants

Reaction Steps

A mixture of 5-chloro-2-(2-methoxy-phenyl)-3-phenethyl-3H-pyrido[4,3-d]pyrimidin-4-one (300 mg, 0.766 mmol), trimethylsilyl chloride (0.097 mL, 0.766 mmol) and sodium iodide (344 mg, 2.297 mmol, 3 equiv.) in propionitrile (7.66 mL) was heated to reflux under nitrogen in the dark for 4 hours. TLC showed no starting material remaining. The reaction mixture was cooled to ambient temperature and poured into 1N NaOH (30 mL). The resulting suspension was extracted with ethyl acetate (3×20 mL), the combined extracts were washed with water, brine and dried, filtered and concentrated in vacuo to give a brown oil. The crude product was purified by column chromatography using 10% ethyl acetate in dichloromethane to provide 235 mg (64%) of product.

Provenance & Evidence