Methods for the synthesis of substituted purines

Details Methods for the synthesis of substituted purines Methods for the synthesis of substituted purines

2005-09-27

2005-09-27

Berch, Mark L. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S264000, C544S276000, C435S004000, C435S091500

Reexamination Certificate

active

06949644

ABSTRACT:
The invention provides general methods for preparing 2,9-, 2,6,9-, O6-aryl- and O6-alkyl-substituted purines in a combinatorial and traceless fashion. The methods involve, in some embodiments, Mitsunobu alkylation of 2-fluoro-6-phenylsulfenylpurine at N9 with alcohols in solution, followed by C2-capture of the purine core with a resin-bound amine and subsequent oxidation and displacement of the C6 sulfonyl group with amines and anilines. In one aspect, the present invention provides a method of preparing a 2,6,9-substituded purine compounds of Formula I:the method comprising:a) oxidizing a resin-bound compound of Formula II:to provide a resin-bound compound of Formula III:b) reacting the compound of Formula III with an amine of Formula IVin-line-formulae description="In-line Formulae" end="lead"?NR3R4  IV,in-line-formulae description="In-line Formulae" end="tail"?to provide a resin-bound compound of Formula Vc) cleaving the resin-bound compound of Formula V from the resin to provide the substituted purine compounds of Formula I.

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