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US 5,206,351 AGranted
Process for the preparation of 2-amino (2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine
AssigneeAsh Stevens, Inc.
InventorsAnica Markovac, Maurice P. LaMontagne
Life of this patent
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Abstract
A process for the preparation of 2-amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl) adenine (V) is described. The process uses a protected 2,6-di(tri-alkylsilylamino)-9-trialkylsilylpurine (II) which is reacted with protected chlorosugar 2,3,5-tri-O-benzyl-1-chloro-D-arabinofuranose (III) and then the protection groups are removed from the 2 and 6 positions. The process provides a 9-beta-D-arabinofuranosyl-2-fluoroadenine (VII) which is an antileukenine drug.
Claims6
A process for the preparation of the compound 2-amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine (V) which comprises:
- (a) reacting 2,6-di(trialkylsilylanino)-9-trialkylsilylpurine (II) with 2,3,5-tri-O-benzyl-1-chloro-D-arabinofuranose (III) wherein alkyl is a lower alkyl group containing 1 to 4 carbon atoms which can be straight chain or branched in a non-polar organic solvent selected from the group consisting of 1,2-dichloroethane and acetonitrile at 80.degree. to 85.degree. C. for at least 18 hours to produce 2,6-di(trialkylsilylamino)-9-(2,3,5-tri-O-benzyl-beta-D-arabino-furanosyl) purine (IV);
- (b) reacting (IV) with a lower alkanol containing 1 to 4 carbon atoms in a second reaction mixture at between about 50.degree.-60.degree. C. for at least 30 minutes to produce 2-amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl) adenine (V);
- and
- (c) separating 2-amino-9-(2,3,5-tri-O-benzyl-beta-D-arabino-furanosyl)adenine (V) from the second reaction mixture wherein the yield is at least 65% based upon the purine (II).
1 more element
Dependencies are inferred from the claim text.