5-Trifluoromethyl-pyrimidine nucleoside

Kobayashi Y, Kumadaki I, Yamamoto K (1977) Simple synthesis of trifluoromethylated pyrimidine nucleosides. J Chem Soc Chem Commun 536-537... 

Trifluridine (5-trifluoromethyl-2 -deoxyuridine) is a fluorinated pyrimidine nucleoside with in vitro inhibitory activity against HSV types 1 and 2, CMV, vaccinia, and some adenoviruses. 

Berber H, Soufyane M, Mirand C, Schmidt S, Aubertin A-M (2001) Synthesis of some cyclic and acyclic nucleoside analogues derived from 4-(trifluoromethyl)pyrimidines. Tetrahedron 57 7369-7376... 

Figure 11. Structures of several S-trifluoromethyl- and 5-pentafluoroethyl-pyrimidine nucleoside analogues.

Trifluoromethylation is the most important perfluoroalkylation reaction. Kobayashi and co-workers reported the trifluoromethylation of aryl, vinyl, alkyl halides with trifluoromethyl iodide in the presence of copper powder in aprotic solvents such as HMPA at 120-150 °C [83,84], and this methodology has been applied to the preparation of fluorinated pyrimidine and purine nucleosides [85,86] (Scheme 27). 

By modifications of known procedures, the following compounds have been prepared l-P-D-arabinofuranosylth3miine,2 -deoxy-5-(trifluoromethyl)-uridine and its a-anomer, a- and p-5-trifluoromethyl-6-aza-2 -deoxyuri-dlnes,l-p-D-arabinofuranosyl-5-fluorouracil,5-fluoro-2 deoxycyti-dine,24 3 -deoxynucleosides of pyrimidines, pyrimidine and purine nucleosides of D-glucuronlc acid, 9-D-mannofuranosyladenlne, 3-P-D-ara-... 

Kobayashi Y, Yamamoto K, Asai T, Nakano M, Kumadaki I (1980) Studies on oiganic fluorine compounds. Part 35. Trifluoromethylation of pyrimidine- and purine-nucleosides with trifluoromethylcopper complex. J Chem Soc Perkin Trans 1 2755-2761... 

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