Collect. Czech. Chem. Commun.
2005, 70, 247-258
https://doi.org/10.1135/cccc20050247
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
Abstract
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.
