2'-Fluorofuranosyl derivatives and methods for preparing 2'-fluoropyrimidine and 2'-fluoropurine nucleosides

US5817799A · kind A · utility

Assignee

• The United States of America, as represented by the Department of Health and Human Services · US

Inventors

• Victor E. Marquez · Gaithersburg, US
• John S. Driscoll · Rockville, US
• Ronald Wysocki · Tucson, US
• Magbool A. Siddiqui · Gaithersburg, US

Key dates

• Filing date: Jul 23, 1990
• Grant date: Oct 6, 1998
• Expiry date: Jul 23, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A method of preparing a 2'-fluoro compound of the formula ##STR1## where B is selected from the group consisting of purines and pyrimidines, both of which may be substituted, comprises reacting a compound of the formula II(a) or II(b) ##STR2## where R and R' are as defined in the specification with an acid halide under conditions effective to obtain a halide of the formula ##STR3## where X is a halogen. A silane of the formula B-Si (R").sub.3 where R" is as defined in the specification, is added to this product (III) under conditions effective to obtain a compound of the formula (IV) ##STR4## The compound of formula (IV) is reacted with a reagent selected from the group consisting of ammonia, BCl.sub.3 and ((C.sub.1 -C.sub.10)alkyl).sub.4 NF, under conditions effective to obtain the compound of formula (I). The compounds of formula (I) resulting from these methods exhibit anti-HIV activities and are useful for therapy against the HIV virus.