Nucleosides, 6-alkylpurine synthesis

With a few notable exceptions—such as puromycin and its relatives, psicofuranine and decoynine, and certain 9-alkylpurines-which will be discussed later, purines and their nucleosides must be anabolized to nucleoside phosphates in order to exert their biological effects. This type of metabolic event has been called a lethal synthesis , because it results in the death of cells that carry it out. 

Reagents A Convenient Route to sec- and tert- 6-Alkylpurines. Tetrahedron Lett. 1996, 37, 1285-1288. (c) Dvorakova, H. Dvorak, D. Holy, A. Synthesis of Acyclic Nucleotide Analogues Derived from 6-(sec- or tert-Alkyl) purines via Coupling of 6-Chloropurine Derivatives with Organocuprates. Collect. Czech. Chem. Commun. 1998, 63, 2065-2074. (d) Hocek, M. Holy, A. Perfluoroalkylation of 6-Iodopurines by Trimethyl(perfluoro-alkyl)silanes. Synthesis of 6-(Perfluoroalkyl)purine Bases, Nucleosides and Acyclic Nucleotide Analogues. Collect. Czech. Chem. Commun. 1999, 64, 229-241. 

The preparation of N-alkylpurines and derivatives encounters problems. When electrophilic alkylation reactions are employed, e.g. methylation, regioisomers are formed. However, in several cases, the Traube synthesis offers a regiospecific or a regioselective route for the synthesis of N-alkylpurines and of related natural products, such as nucleosides. 

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