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Substituted pyrimidines. II. 1,3‐Dimethylisocytosine and related compounds
Author(s) -
Maehr Hubert,
Smallheer Joanne,
Toome Voldemar
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140433
Subject(s) - chemistry , pyrimidine , methylation , thio , medicinal chemistry , stereochemistry , biochemistry , dna
1,3‐Dimethyl‐1,2‐dihydro‐2‐imino‐4(3 H )pyrimidinone (1,3‐dimethylisocytosine) was prepared by methylation of 2‐amino‐3‐methyl‐4(3 H )pyrimidinone and was degraded in alkaline solution to a mixture of 3‐methyl‐2‐methylamino‐4(3 H )pyrimidinone, 1,3‐dimethyl‐2,4‐(1 H ,3 H )pyrimid‐indione, 2‐methylamino‐l‐methyl‐4(1 H )pyrimidinone, 1‐methyl‐2,4‐(1 H ,3 H )pyrimidindione and 3‐methyl‐2,4‐(1 H ,3 H )pyrimidindione. Thiation of the title compound gave both 1,2‐dihydro‐1,3‐dimethyl‐2‐thio‐4(3 H )pyrimidinone and 1,3‐dimethyl‐2,4‐(1 H ,3H)pyrimidinedithione. The title compound is a tautomerically fixed pyrimidine and its uv spectra were compared with related compounds, notably 3‐methyl‐2‐dimethylarnino‐4(3 H )pyrimidinone which is also tautomerically fixed.