title: Direct C-H arylation of purine on solid phase and its use for chemical libraries synthesis.
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.
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Institute of Molecular and Translational Medicine, University of Palacký, Olomouc, Czech Republic.
authors.forename: Barbora
authors.initials: B
authors.lastname: Vanková
authors.forename: Viktor
authors.initials: V
authors.lastname: Krchnák
authors.forename: Miroslav
authors.initials: M
authors.lastname: Soural
authors.forename: Jan
authors.initials: J
authors.lastname: Hlavác
mesh_terms: D015394:Molecular Structure; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D013237:Stereoisomerism
chemical_list: D011687:Purines; D054852:Small Molecule Libraries