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Paper | Regular issue | Vol 27, No. 3, 1988, pp.769-774
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4417
Synthesis of 3-Substituted 3,4-Dihydropyrimidines: N-Alkoxycarbonylation with Trichloromethyl Chloroformate and Alcohols

Hidetsura Cho,* Akira Mizuno, Keiyuu Shima, Masaru Ueda, Yumi Takeuchi, Mikiko Hamaguchi, and Nobuaki Taniguchi

*The Institute of Food Chemistry, 1-1-1, Wakayamadai, Shimamotocho, Mishimagun, Osaka 618-0024, Japan


N-Alkoxycarbonylation reactions of dihydropyrimidines with trichloromethyl chloroformate (phosgene dimer) and an alcohol were carried out in order to obtain the dihydropyrimidines with a complicated alkyl qroup or an alkyl group containing a nitrogen atom. Especially, the synthetically difficult problem of the unstable N-substituted dihydropyrimidines containing a nitrogen atom in an ester group was overcome by the method II: 0.5-1.2 mol equiv. of phosgene dimer, 1.0-6.0 equiv. of tertiary aminoalcohol, and 6 equiv. of Et3N in THF at -23°C-r.t.