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  • Title: Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines.
    Author: Taddei D, Kilian P, Slawin AM, Derek Woollins J.
    Journal: Org Biomol Chem; 2004 Mar 07; 2(5):665-70. PubMed ID: 14985806.
    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.
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