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Issue 5, 2004
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Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines

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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.

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

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Publication details

The article was received on 10 Oct 2003, accepted on 16 Dec 2003 and first published on 27 Jan 2004


Article type: Paper
DOI: 10.1039/B312629C
Citation: Org. Biomol. Chem., 2004,2, 665-670
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    Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines

    D. Taddei, P. Kilian, A. M. Z. Slawin and J. Derek Woollins, Org. Biomol. Chem., 2004, 2, 665
    DOI: 10.1039/B312629C

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