Collect. Czech. Chem. Commun. 1999, 64, 229-241

Perfluoroalkylation of 6-Iodopurines by Trimethyl(perfluoroalkyl)silanes. Synthesis of 6-(Perfluoroalkyl)purine Bases, Nucleosides and Acyclic Nucleotide Analogues

Michal Hocek* and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


A CuI/KF mediated perfluoroalkylation reaction of various 9-substituted 6-iodopurines 1 with trimethyl(trifluoromethyl)silane or heptafluoropropyl(trimethyl)silane was used for the synthesis of the corresponding 6-(trifluoromethyl)- and 6-(heptafluoropropyl)purine derivatives (purine bases, nucleosides and acyclic nucleotide analogues) in moderate to good yields.

Keywords: Purines; Nucleosides; Cross-coupling reactions; Trifluoromethylation; Perfluoroalkylation; Cuprates; Fluorinated compounds; Cytostatic activity.