Palladium-Catalyzed Animation of 6-Chloropurine. Synthesis of N⁶-Substituted Adenosine Analogues

Judith Barends Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018, WS Amsterdam, The Netherlands

Johannes B. van der Linden Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018, WS Amsterdam, The Netherlands

Floris L. Van Delft Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018, WS Amsterdam, The Netherlands

Gerrit-Jan Koomen Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018, WS Amsterdam, The Netherlands

Abstract

Room-temperature treatment of persilylated 6-chloro-9-β-D-ribofuranosyl-purine with a variety of aliphatic and aromatic amines, in the presence of Pd₂(dba)₃, BINAP and base, leads to N⁶-substituted adenosine analogues in fair to good yields. Coupling of chloropurine with a chiral aziridinyl diester is applied in the synthesis of a potential adenylosuccinate lyase inhibitor.

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Palladium-Catalyzed Animation of 6-Chloropurine. Synthesis of N⁶-Substituted Adenosine Analogues

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Palladium-Catalyzed Animation of 6-Chloropurine. Synthesis of N6-Substituted Adenosine Analogues

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Palladium-Catalyzed Animation of 6-Chloropurine. Synthesis of N⁶-Substituted Adenosine Analogues