1987•Journal of Heterocyclic ChemistryRequires access

Further study on 1,3‐dialkylaminouracil with dimethyl acetylenedicarboxylate

Tsuneo Itoh, Ikuko Fujii, Y. TOMII, Haruo Ogura, Yoshihisa Mizuno, Norio Kawahara

Abstract

Abstract On the treatment of 1,3‐dialkyl‐6‐alkylaminouracil (1) with dimethyl acetylenedicarboxylate (DMAD), we were able to develop a new synthesis of deazapurine (pyrrolo[2,3‐d]pyrimidine, 4), and proposed the plausible mechanism for the formation of 3 and 4 from the adduct [dimethyl 2‐(1,3‐dialkyl‐6‐alkylamino‐2,4‐dioxopyrimidin‐5‐yl)fumarate, 2] of 1 with DMAD.

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Available abstract

Key concepts: Dimethyl acetylenedicarboxylate, Chemistry, Adduct, Pyrimidine, Medicinal chemistry, Dimethyl fumarate, Stereochemistry, Organic chemistry