Iodoethane → 2-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinonitrile

Participants

Reaction Steps

Sodium methoxide (155 mg, 2.87 mmol) was added to a suspension of 2-amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile (400 mg, 1.44 mmol) in methanol (8 ml) at room temperature in a nitrogen atmosphere, followed by stirring. After 15 minutes, iodoethane (0.35 ml, 4.38 mmol) was added thereto, followed by stirring as it was. After 15 hours, additional iodoethane (0.35 ml, 4.38 mmol) was added thereto, and the mixture was further stirred. After 24 hours, the reaction solution was concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=2:1, 1:2, 1:5). The resulting crude objective compound was suspended in diethyl ether, and then the solid was collected by filtration and washed with diethyl ether, to give the title compound (149 mg, 34%) as a pale yellow solid.

Provenance & Evidence