Synthetic Studies on Formamidopyrimidines Related to Clofarabine

William R. Cantrell, Dennis Lovett, Tracy Engles, Bruce Anderson, William E. Bauta, Paul C. Wolstenholme-Hogg
2008 Nucleosides, Nucleotides & Nucleic Acids  
2 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 C 1 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
more » ... h allyl chloroformate, followed by deprotection of the alloc group with catalytic Pd(PPh 3 ) 4 and dimedone. A synthesis of compound 6 from 4 is also described.
doi:10.1080/15257770802257770 pmid:18696361 fatcat:tqyuhwys7jgn5o5f5ifqxpnmoa