Heterocyclic polyfluoro-compounds. Part X. Nucleophilic substitution in tetrafluoropyrimidine
- 1 January 1967
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 1822-1826
- https://doi.org/10.1039/j39670001822
Abstract
Tetrafluoropyrimidine, prepared in high yield by reaction of tetrachloropyrimidine with anhydrous potassium fluoride at elevated temperatures, is highly susceptible to attack by nucleophiles; the ease of displacement of ring fluorines decreases in the order 4- and 6- > 2- 5-. Through use of appropriate nucleophilic reagents the following fluoro-pyrimidines have been prepared: 4-X·C4F3N2(X = OH), 4-Y·C4F3N2, and 4,6-Y2·C4F2N2(Y = NH2, OMe, NHPh, NHMe, or NMe2), and 2,4,6-Z3·C4FN2(Z = OMe). The structures of these compounds were established by nuclear magnetic resonance spectroscopy. Interpretation of the orientation of nucleophilic attack on tetrafluoropyrimidine and on pentafluoropyridine is provided.Keywords
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