Synthesis of quinazoline derivatives through anionic cycloaddition reactions of methyl 2,4-dimethoxy-6-methyl-5-pyrimidinecarboxylate with acetylenes and olefins

The anionic cycloaddition of methyl 2,4-dimethoxy-6-methyl-5-pyrimidinecarboxylate has been investigated. The lithium salt of methyl 2,4-dimethoxy-6-methyl-5-pyrimidinecarboxylate, generated by deprotonation with lithium diisopropylamide in ether at – 70°, reacted smoothly with electron deficient acetylenes and olefins to give quinazoline derivatives in a single step.