Collect. Czech. Chem. Commun. 1998, 63, 2065-2074

Synthesis of Acyclic Nucleotide Analogues Derived from 6-(sec- or tert-Alkyl)purines via Coupling of 6-Chloropurine Derivatives with Organocuprates

Hana Dvořákováa, Dalimil Dvořákb and Antonín Holýa

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
b Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic


Coupling of 9-[2-(diisopropyloxyphosphonylmethoxy)ethyl]-6-chloropurine (23) (and (R)-9-[2-(diisopropyloxyphosphonylmethoxy)propyl]-6-chloropurine (24), respectively) with organocuprates derived from Grignard reagents afforded after deprotection 6-(sec- or tert-alkyl) substituted phosphonates 31-36. As a model a series of 6-(sec- or tert-alkyl)purines 2-12 was also prepared.

Keywords: Acyclic nucleoside phosphonates; Phosphonomethoxyalkylpurine derivatives; 6-Alkylpurines; Purines; Organocopper reagents; Cross-coupling reactions.