title: Synthetic studies on formamidopyrimidines related to clofarabine.
abstract: Degradation of clofarabine (3) in 0.9% saline solution at 100 degrees 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 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.
authors.affiliation: Genzyme Corporation, Quality and Technical Operations, San Antonio, Texas78229, USA.
authors.forename: William R
authors.initials: WR
authors.lastname: Cantrell
authors.forename: Dennis
authors.initials: D
authors.lastname: Lovett
authors.forename: Tracy
authors.initials: T
authors.lastname: Engles
authors.forename: Bruce
authors.initials: B
authors.lastname: Anderson
authors.forename: William E
authors.initials: WE
authors.lastname: Bauta
authors.forename: Paul C
authors.initials: PC
authors.lastname: Wolstenholme-Hogg
mesh_terms: D000227:Adenine Nucleotides / Q000737:chemistry*; D001087:Arabinonucleosides / Q000737:chemistry*; D000077866:Clofarabine; D005559:Formamides / Q000138:chemical synthesis*; D005561:Formates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000138:chemical synthesis*
chemical_list: D000227:Adenine Nucleotides; D001087:Arabinonucleosides; D005559:Formamides; D005561:Formates; D011743:Pyrimidines; D000077866:Clofarabine; C042113:allyl chloroformate