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US 5,180,824 AGranted
6-azido-2-fluoropurine, useful in the synthesis of nucleosides
AssigneeBerlex Biosciences
InventorsJohn G. Bauman, Randolph C. Wirsching
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Abstract
This invention pertains to novel methods of synthesizing fludarabine, fludarabine phosphate and related nucleoside pharmacologic agents utilizing 6-azido-2-fluoropurine as a novel intermediate. In particular this invention pertains to a synthesis of fludarabine where the relatively low yield fluorination step is done before the costly coupling step.
Claims16
A compound 6-azido-2-fluoropurine, with the structure:
- ##STR10##
A method for preparing 6-azido-2-fluoropurine comprising the following steps:
- (a) reacting 2-amino-6-chloropurine with an alkali metal azide to yield 2-amino-6-azidopurine;
- and
- (b) diazotizing and fluorinating 2-amino-6-azidopurine to yield 6-azido-2-fluoropurine.
A method for preparing 2-fluoradenine comprising the following steps:
- (a) reacting 2-amino-6-chloropurine with an alkali metal azide to yield 2-amino-6-azidopurine;
- (b) diazotizing and fluorinating 2-amino-6-azidopurine to yield 6-azido-2-fluoropurine;
- and
- (c) reducing 6-azido-2-fluoropurine to yield 2-fluoroadenine.
1 more element
Dependencies are inferred from the claim text.