Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines.

D Taddei, Petr Kilian, Alexandra Martha Zoya Slawin, John Derek Woollins

Research output: Other contribution

22 Citations (Scopus)

Abstract

A simple and efficient synthesis of 6-chloro-2-iodopurine from hypoxanthine has been achieved. This strategy relied on a regiospecific lithiation/quenching sequence of 6-chloro-9-(tetrahydropyran-2-yl) purine using Harpoon's base and tributyltin chloride. HMBC NMR studies on the product and intermediates confirmed the regioselectivity of this methodology. The molecular structures of the final dihalogenopurine and its 9-protected precursor were determined by single crystal X-ray diffraction.

Original languageEnglish
Volume2
DOIs
Publication statusPublished - 2004

Keywords

  • HUMAN-IMMUNODEFICIENCY-VIRUS
  • DEPENDENT KINASE INHIBITORS
  • 2,6,9-TRISUBSTITUTED PURINES
  • ANTIVIRAL ACTIVITY
  • CDK INHIBITORS
  • DERIVATIVES
  • NUCLEOSIDES
  • LIBRARIES
  • ADENOSINE
  • DEOXYNUCLEOSIDES

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