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Communication | Regular issue | Vol 22, No. 3, 1984, pp.493-496
Published online, 1st January, 1970
DOI: 10.3987/R-1984-03-0493
Synthesis of Furo[3,4-d]pyrimidine Derivatives Using Ethyl 4-Bromoacetoacetate

Takuo Chiba,* Hirotoshi Sato, and Tetsuzo Kato

*Pharmaceutical Institute, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan


Reaction of ethyl 4-bromoacetoacetate (1) with benzaldehyde (2a) and urea in the presence of hydrochloric acid gave 6-bromomethyl-5-ethoxycarbonyl-4-phenyl-3,4-dihydro-2(1H)-pyrimidinone (3a). Similarly, reaction of 1 and urea with p-anisaldehyde (2b), p-hydroxybenzaldehyde (2c), and furfural (2d) afforded the corresponding 6-bromomethyl-3,4-dihydro-2(1H)-pyrimidinones 3b-3d. Thermolysis of compounds 3a-3d gave rise to the corresponding 4,7-dihydrofuro[3,4-d]pyrimidine-2,5(1H,3H)-diones 4a-4d.