Efficient synthesis of unprotected C-5-aryl/heteroaryl-2'-deoxyuridine via a Suzuki-Miyaura reaction in aqueous media

Molecules. 2012 Dec 5;17(12):14409-17. doi: 10.3390/molecules171214409.

Abstract

Following our previous results on an environmentally benign one-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides under aqueous conditions, we investigate herein the Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl derivatives at the C5 position of unprotected 2'-deoxyuridine in the same media with a common catalyst system avoiding exotic ligands, since palladium acetate and triphenylphosphine afforded the expected products in moderate to good yields.

MeSH terms

  • Boronic Acids / chemistry
  • Catalysis
  • Deoxyuridine / analysis*
  • Deoxyuridine / chemical synthesis*
  • Idoxuridine / chemistry*
  • Ligands
  • Magnetic Resonance Imaging
  • Molecular Structure
  • Organophosphorus Compounds / analysis
  • Organophosphorus Compounds / chemistry
  • Palladium / analysis
  • Palladium / chemistry
  • Water / analysis

Substances

  • 4-methoxyphenylboronic acid
  • Boronic Acids
  • Ligands
  • Organophosphorus Compounds
  • Water
  • triphenylphosphine
  • Palladium
  • Idoxuridine
  • Deoxyuridine