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Pyrimidines. XIII. 2‐ and 6‐substituted 4‐pyrimidinecarboxylic acids
Author(s) -
Daves G. Doyle,
O'Brien Darrell E.,
Lewis Leland R.,
Cheng C. C.
Publication year - 1964
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.5570010305
Subject(s) - chemistry , nitrous acid , thio , amino acid , organic chemistry , medicinal chemistry , biochemistry
Abstract The “abnormal” behavior of 4,6‐dimethyl‐2‐pyrimidinol towards nitrous acid has been clarified. The reaction between 4‐methyl‐2‐pyrimidinol and nitrous acid has been utilized as a new synthetic procedure for the preparation of several 2‐substituted 4‐pyrimidinecarboxylic acids. 2‐Hydroxy‐4‐pyrimidinecarboxylic acid has also been prepared from 4‐chloro‐2‐methylthiopyrimidine via the trimethylammonium intermediate. 6‐Amino‐ and 6‐thio‐4‐pyrimidinecarboxylic acids have been readily prepared from the previously reported 6‐hydroxy‐4‐pyrimidinecarboxylic acid.