title: Synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, an impurity of acyclovir.
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.
authors: Fine Chemicals Pilot Plant Facility, University of Alcalá, 28871 Alcalá de Henares, Madrid, Spain.
authors: Rosa M
authors: RM
authors: Suárez
authors: Maria Paz
authors: MP
authors: Matía
authors: José Luis
authors: JL
authors: Novella
authors: Andres
authors: A
authors: Molina
authors: Antonio
authors: A
authors: Cosme
authors: Juan José
authors: JJ
authors: Vaquero
authors: Julio
authors: J
authors: Alvarez-Builla
mesh_terms: D015075:2-Aminopurine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000212:Acyclovir / Q000138:chemical synthesis*; D000478:Alkylation; D001557:Benzenesulfonates / Q000737:chemistry; D002384:Catalysis; D004340:Drug Contamination; D019855:Ethylene Glycol / Q000737:chemistry; D005557:Formaldehyde / Q000737:chemistry; D006851:Hydrochloric Acid / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry
chemical_list: C573194:4-methylbenzenesulfonic acid; C576542:9,9'-(1,2-ethanediylbis(oxymethylene))bis-2-amino-1,9-dihydro-6H-purin-6-one; D001557:Benzenesulfonates; D011108:Polymers; D000644:Quaternary Ammonium Compounds; D005557:Formaldehyde; D015075:2-Aminopurine; C009405:tetrabutylammonium; D019855:Ethylene Glycol; D006851:Hydrochloric Acid; D000212:Acyclovir; C003043:paraform