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Paper | Regular issue | Vol 78, No. 5, 2009, pp.1205-1216
Published online, 15th January, 2009
DOI: 10.3987/COM-08-11596
Copper-Mediated N-Arylation in the Synthesis of Aryladenines

Jan Krouželka and Igor Linhart*

*Department of Organic Chemistry, Institute of Chemical Technology Prague, 166 28 Prague, Technická 1905, Czech Republic

Abstract

A series of N3 and N9 aryladenines was prepared by arylation of 8-bromoadenine under modified Chan-Lam-Evans coupling conditions followed by reductive debromination with hydrogen on palladium. Conditions of arylation were optimised to maximise the yield of N3-arylated products. The selectivity of the reaction varied with temperature the ligand used. The best results were obtained in DMF with phenanthroline as a ligand at 60°C.