Facile and efficient access to 2, 6, 9-tri-substituted purines through sequential N9, N2 Mitsunobu reactions

S Fletcher, VM Shahani, PT Gunning

Index: Fletcher, Steven; Shahani, Vijay M.; Gunning, Patrick T. Tetrahedron Letters, 2009 , vol. 50, # 29 p. 4258 - 4261

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Citation Number: 29

Abstract

A facile, efficient and mild synthesis of 2, 6, 9-tri-substituted purines is presented, starting from commercially available 2-amino-6-chloropurine, which employs sequential N9 then N2 Mitsunobu reactions as key steps. Importantly, our synthetic approach to N2- functionalization of the purine nucleus obviates the harsh conditions required by the traditional nucleophilic aromatic substitution of a 2-halo group with primary amines. ...