Direct C-H arylation of purine on solid phase and its use for chemical libraries synthesis

ACS Comb Sci. 2011 Sep 12;13(5):496-500. doi: 10.1021/co200075r. Epub 2011 Jun 30.

Abstract

C(8)-H direct arylation of purine derivatives immobilized on Wang resin is described. The purine skeleton was immobilized via C(6)-regioselective substitution of 2,6-dichloropurine with polymer-supported amines. After N(9)-alkylation with two different alkyl iodides and C(2) substitution with two selected amines, reaction conditions for C(8)-H arylation were developed and optimized. Various aryl bromides and aryl iodides were used for the reaction affording the target 2,6,8,9-tetrasubstituted purines in very good purity. The same reaction conditions were also applied for the synthesis of 2,6,8-trisubstituted purines, however, yields were lower. The methodology is applicable for high throughput synthesis of chemical libraries comprised of purine scaffold.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Purines / chemical synthesis*
  • Purines / chemistry
  • Small Molecule Libraries / chemical synthesis*
  • Small Molecule Libraries / chemistry
  • Solid-Phase Synthesis Techniques / methods*
  • Stereoisomerism

Substances

  • Purines
  • Small Molecule Libraries