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The structure of some methyl and benzyl malonate derivatives of pyrimidine
Author(s) -
Reynolds G. Fredric,
Fenwick Marc B.
Publication year - 1980
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.5570170334
Subject(s) - chemistry , pyrimidine , malonate , solvent , sodium , medicinal chemistry , nuclear magnetic resonance spectroscopy , sodium salt , ion , spectroscopy , molecule , diethyl malonate , organic chemistry , stereochemistry , inorganic chemistry , catalysis , physics , quantum mechanics
Reaction of 2,4,6‐trichloropyrimidine with sodium dibenzylmalonate in p ‐dioxane gave 4,6‐dichloro‐2‐(dibenzylmalonyl)pyrimidine, while reaction of 2,4,6‐trichloropyrimidine with sodium dimethylmalonate yielded both 4,6‐dichloro‐2‐(dimethylmalonyl)pyrimidine and 2,2‐bis‐(4,6‐dichloropyrimidin‐2‐yl)dimethylmalonate. Structural studies using nmr, ir and uv spectroscopy indicate that for the former two compounds in basic solvent, an equilibrium exists between the keto forms and resonance‐stabilized enolate ions.