Synthesis and full characterisation of 6-chloro-2-iodopurine, a template for the functionalisation of purines.
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.
Taddei
David
D
Department of Chemistry, University of St Andrews, St Andrews, Scotland.
Kilian
Petr
P
Slawin
Alexandra M Z
AM
Derek Woollins
J
J
D018360:Crystallography, X-Ray; D018844:Cyclin-Dependent Kinases / Q000037:antagonists & inhibitors; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D019271:Hypoxanthine / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
C494671:6-chloro-2-iodopurine; D004791:Enzyme Inhibitors; D011687:Purines; D019271:Hypoxanthine; D018844:Cyclin-Dependent Kinases