3-Aminopyridine → Methyl 2-cyano-3-(methylsulfanyl)-3-(3-pyridinylamino)-2-propenoate

Participants

Reaction Conditions

Reaction Steps

1.39 g (14.8 mmol) of 3-aminopyridine are dissolved in 50 ml of THF, cooled to −20° C., and 7.4 ml of a 2M solution of n-butyllithium in hexane are added. After stirring for 15 min, 2.00 g (9.84 mmol) of methyl 3,3-bis(methylthio)-2-cyanoacrylate are added. The mixture is warmed to room temperature while stirring and then hydrolyzed with ice-water. The product is extracted with dichloromethane. After drying over sodium sulfate, the solvent is removed in vacuo and the residue is purified by preparative HPLC. 0.44 g (18.1% of theory) of the desired product is obtained.

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