Selective synthesis of 7-substituted purines via 7,8-dihydropurines

Org Lett. 2010 Dec 17;12(24):5724-7. doi: 10.1021/ol1025525. Epub 2010 Nov 19.

Abstract

A simple and efficient protocol for the preparation of 7-substituted purines is described. 6- and 2,6-Dihalopurines were N(9)-tritylated and then transformed to 7,8-dihydropurines by DIBAL-H. Subsequent N(7)-alkylation followed by N(9)-trityl deprotection with trifluoroacetic acid was accompanied by spontaneous reoxidation, which led to the 7-substituted purines at 55-88% overall isolated yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Hydrogen / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Purines / chemical synthesis*

Substances

  • Purines
  • Hydrogen