Collect. Czech. Chem. Commun. 2005, 70, 247-258

Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines

Dana Hocková*, Milena Masojídková and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-166 10, Prague 6, Czech Republic


Several 6-[(phosphonomethoxy)alkyl]pyrimidines and 6-[(phosphonomethoxy)alkynyl]pyrimidines were prepared as saturated and unsaturated carba-analogues of antivirally active 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidine. As the key step of their synthesis the Sonogashira cross-coupling reaction was successfully applied. The replacement of the C-O moiety by the C-C bond resulted in the loss of biological activity.

Keywords: Nucleotide analogues; Acyclic nucleoside phosphonates; Pyrimidines; Sonogashira reaction; Cross-coupling reactions; Nucleosides; Alkynes; Hydrogenation; Antivirals.

References: 16 live references.