Direct C-H arylation of purine on solid phase and its use for chemical libraries synthesis
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
21675766
DOI
10.1021/co200075r
Knihovny.cz E-resources
- MeSH
- Small Molecule Libraries chemical synthesis chemistry MeSH
- Molecular Structure MeSH
- Purines chemical synthesis chemistry MeSH
- Stereoisomerism MeSH
- Solid-Phase Synthesis Techniques methods MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Small Molecule Libraries MeSH
- Purines MeSH
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.
References provided by Crossref.org
