Synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, an impurity of acyclovir

Molecules. 2012 Jul 25;17(8):8735-41. doi: 10.3390/molecules17088735.

Abstract

The synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, a minor impurity of acyclovir, is described. Starting with commercial N-(9-acetyl-6-oxo-1H-purin-2-yl)acetamide, the process uses an acid catalysed phase transfer catalysis (PTC) process to produce the selective alkylation at the 9 position of the guanine ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Aminopurine / analogs & derivatives*
  • 2-Aminopurine / chemical synthesis
  • Acyclovir / chemical synthesis*
  • Alkylation
  • Benzenesulfonates / chemistry
  • Catalysis
  • Drug Contamination*
  • Ethylene Glycol / chemistry
  • Formaldehyde / chemistry
  • Hydrochloric Acid / chemistry
  • Polymers / chemistry
  • Quaternary Ammonium Compounds / chemistry

Substances

  • 4-methylbenzenesulfonic acid
  • 9,9'-(1,2-ethanediylbis(oxymethylene))bis-2-amino-1,9-dihydro-6H-purin-6-one
  • Benzenesulfonates
  • Polymers
  • Quaternary Ammonium Compounds
  • Formaldehyde
  • 2-Aminopurine
  • tetrabutylammonium
  • Ethylene Glycol
  • Hydrochloric Acid
  • Acyclovir
  • paraform