Document Type
Article
Disciplines
Biochemistry
Abstract
Ring-chlorination of 6-trifluoromethyluracil in phosphorus oxychloride in the presence of triethyl, tri-npropyl, and tri-n-butylamines was studied with respect to by-product formation. Comparisons were made with the results obtained by treating the preformed chlorinated pyrimidine with triethyl amine in boiling toluene. Amination of chloropyrimidines by tertiary amines takes place by a Hofmann type reaction with substituent orientation generally in the 2 position of the ring. Yields of products depended on the base and reaction time. The rate of substitution in the 2 position is significantly enhanced by the presence of the trifluoromethyl group in the 6 position as compared with a methyl group. Heating preformed chloropyrimidines with tertiary amines in toluene, offers a satisfactory approach for the preparation of 2-N,N-disubstituted aminopyrimidines. For the formation of ring-chlorinated pyrimidines in phosphorus oxychloride with a minimum of by-products, tri-n-propylamine, after a short reflux period is most useful
Article Number
1017
Publication Date
1987
Recommended Citation
Gershon, Herman; Grefig, Anthony T.; and Clarke, Donald Dudley PhD, "Pyrimidines. 9. chlorination of 6-trifluoromethyluracil with phosphorus oxychloride in the presence of trialkylamines / Herman Gershon [ab], Anthony T. Grefig [a], and Donald D. Clarke [b] [a] Boyce Thompson Institute for Plant Research at Cornell University, Ithaca, New York 14853 [b] Department of Chemistry, Fordham University, Bronx, New York 10458" (1987). Chemistry Faculty Publications. 18.
https://research.library.fordham.edu/chem_facultypubs/18
Comments
Journal of heterocyclic chemistry. 24:1243-1247. http://dx.doi.org/10.1002/jhet.5570240502