Pyridine-4-amidine hydrochloride → 5-(4-Chlorophenyl)-2-pyridin-4-ylpyrimidine

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Reaction Steps

Isonicotinamidine, hydrochloride (0.488 g) and 2-(4-chlorophenyl)malondialdehyde (0.566 g) were combined in anhydrous pyridine (10 ml) and heated to reflux under nitrogen, for 18 h. The resultant dark solution was cooled and poured onto ice-water (150 ml) and the mixture extracted with ethyl acetate (150 ml, then 50 ml). The combined organic extracts were washed with water (3×10 ml), saturated brine (20 ml), dried (Na2SO4), evaporated to dryness under reduced pressure and the residue purified by silica gel column chromatography with 3.5% methanol/dichloromethane as eluent, to give the title compound as a white solid (0.463 g, 56%).

Provenance & Evidence