Investigation of the Chlorination of 4-(Perfluoroalkyl)-5-(p-toluenesulfonyl)uracils. Synthesis of 5-Chloro-6-(perfluoroalkyl)-5-(p-toluenesulfonyl)pyrimidine-2,4(3H,5H)-diones

doi:10.1007/s10593-013-1286-1

Paper

Investigation of the Chlorination of 4-(Perfluoroalkyl)-5-(p-toluenesulfonyl)uracils. Synthesis of 5-Chloro-6-(perfluoroalkyl)-5-(p-toluenesulfonyl)pyrimidine-2,4(3H,5H)-diones

Published Jul 12, 2013 · A. Gudz, A. S. Kanishchev, Y. Vlasenko

Chemistry of Heterocyclic Compounds

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Abstract

Chlorination of 4-(perfluoroalkyl)-5-(p-toluenesulfonyl)-2,6-bis(trimethylsilyloxy)pyrimidines led to the formation of 5-chloro-6-(perfluoroalkyl)-5-(p-toluenesulfonyl)pyrimidine-2,4(3H,5H)-diones, the structure of which was confirmed by NMR spectroscopy and X-ray structural analysis. The reactions of chlorinated pyrimidine-2,4(3H,5H)-diones with nucleophiles were investigated.

Study Snapshot

Chlorination of 4-(perfluoroalkyl)-5-(p-toluenesulfonyl)-2,6-bis(trimethylsilyloxy)pyrimidines led to the formation of 5-chloro-6-(perfluoroalkyl)-5

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Investigation of the Chlorination of 4-(Perfluoroalkyl)-5-(p-toluenesulfonyl)uracils. Synthesis of 5-Chloro-6-(perfluoroalkyl)-5-(p-toluenesulfonyl)pyrimidine-2,4(3H,5H)-diones

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References

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New nucleoside analogs based on polyfluoroalkyl-substituted 1,2,3-triazoles show high selectivity indices for cytotoxicity and anti-Epstein-Barr virus activity.

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The new green glycosylation condition efficiently prepares trifluorothymidine 1 at large-scale without CHCl3 or transition-metal catalysts, making it suitable for process development of active pharmaceutical ingredients.

Treatment of Polyfluoro‐1,1‐dihydroalkyl Sulfones with Sodium Cyanate and Triethylamine: A New Method for the Synthesis of 6‐(Polyfluoroalkyl)uracils

This study presents a new method for the synthesis of 6-(polyfluoroalkyl)uracils using polyfluoro-1,1-dihydroalkyl benzyl sulfones and sodium cyanate in the presence of triethylamine.

6-Substituted and 5,6-disubstituted derivatives of uridine: stereoselective synthesis, interaction with uridine phosphorylase, and in vitro antitumor activity.

6-alkyluridines show potential antitumor activity, with 5-fluoro-6-(fluoromethyl)uridine showing cytotoxicities comparable to 5-fluorouracil.

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Uranium reacts with hypochlorous acid to produce trichloroacetic acid, carbon dioxide, and nitrogen trichloride, with 5-chlorouracil also degrading to trichloroacetic acid.

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The best inhibitor of thymidine phosphorylase is 5-phenylbutyl-6-(trifluoromethyl)uracil (XI), which is 67-fold better than 6-methyluracil and 23-fold better than 6-methyl-5-(phenylazo)uracil.

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