Reaction of 2-Cyanopyrimidine Derivatives with Nucleophilic Reagents.

Since the reaction of sodium methoxide with 4-chloro-6-methylpyrimidine-2-carbonitrile afforded 2, 4-dimethoxy-6-methylpyrimidine, the cyano group in 2-and 4-positions of the pyrimidine ring is fairly active to nucleophilic reagents. Reaction with 2-cyanopyrimidine derivatives showed that the substitution of cyano group with alkoxide ion decreased in the order to primary, secondary, and tertiary alkyls. This reaction did not take place when the alkoxide ion was replaced with phenoxide or thiophenoxide ion, forming acid amide alone. Application of sodium ethoxide to 2-cyanoquinoline, 4-cyano-quinoline, and 4-cyanoacridine failed to produce any ethoxylated derivatives.