Studies on Pyrimidine Derivatives. IX. Coupling Reaction of Monosubstituted Acetylenes with Iodopyrimidines

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The pyrimidine derivatives containing an acetylenic side chain were synthesized by means of the reaction of alkyl-(or phenyl) acetylenes with twelve kinds of 2-, 4-, and 5-iodopyrimidines in the presence of a palladium triphenylphosphine complex in satisfactory yields. When propargyl alcohol was used, the reaction exhibited the tendency of decreasing the yield. The reaction readily proceeded in both 2, 4-diiodo- and 4, 6-diiodo-pyrimidines to give the corresponding dialkynyl derivatives. This acetylene coupling reaction was applicable to the synthesis of the 4-quinazoline derivatives.