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Degradation of clofarabine (3) in 0.9% saline solution at 100°C afforded three degradation products which were determined to be formamidopyrimidines 4-6.Compounds 4 and 5 were assigned as C1' anomers on the basis of one-dimensional and two-dimensional NMR experiments, whereas 6 was found to be the formamidopyrimidine lacking the sugar moiety. An improved procedure for the synthesis of formamidopyrimidines was developed, wherein benzoylated clofarabine (11) was treated with allyl chloroformate, followed by deprotection of the alloc group with catalytic Pd(PPh3)4 and dimedone. A synthesis of compound 6 from 4 is also described. [ABSTRACT FROM AUTHOR]

Abstract: Addition of aqueous hydrogen peroxide significantly accelerates the substitution reactions of hydroxide salts with haloarenes bearing electron withdrawing substituents. A similar effect is observed in the reactions of hydroxide salts with halogenated heteroarenes. Reactions are carried out in water or water–THF at ambient temperature or at 50–60°C. [Copyright &y& Elsevier]