title: Convenient syntheses of 6-methylpurine and related nucleosides.
abstract: Efficient methods for the synthesis of 6-methylpurine (3), 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-methylpurine (8), and 6-methyl-9-beta-D-ribofuranosylpurine (5) are described. Methodology involving the (Ph3P)4Pd catalyzed cross-coupling reaction of CH3ZnBr with several different 6-chloropurine derivatives is described in high yield. This methodology now provides a facile and high-yielding synthesis of 8, which is needed in significant amounts for studies in cancer gene therapy.
authors.affiliation: Organic Chemistry Department, Southern Research Institute, Birmingham, AL 35255-5305, USA.
authors.forename: A E
authors.initials: AE
authors.lastname: Hassan
authors.forename: R A
authors.initials: RA
authors.lastname: Abou-Elkair
authors.forename: J A
authors.initials: JA
authors.lastname: Montgomery
authors.forename: J A
authors.initials: JA
authors.lastname: Secrist
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001965:Bromides / Q000138:chemical synthesis; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000138:chemical synthesis*; D009705:Nucleosides / Q000138:chemical synthesis*; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D011687:Purines / Q000138:chemical synthesis*; D017967:Zinc Compounds / Q000138:chemical synthesis
chemical_list: C421304:9-(2-deoxy-erythro-pentofuranosyl)-6-methylpurine; D000970:Antineoplastic Agents; D001965:Bromides; D009005:Monosaccharides; D009705:Nucleosides; D011684:Purine Nucleosides; D011687:Purines; D017967:Zinc Compounds; C034051:6-methylpurine riboside; C016588:6-methylpurine; C093802:zinc bromide