Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir

The synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, a minor impurity of acyclovir, is described.<em> </em>Starting with commercial <em>N</em>-(9-acetyl-6-o...

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Main Authors: Juan José Vaquero, Antonio Cosme, Andres Molina, José Luis Novella, Maria Paz Matía, Rosa M. Suárez, Julio Alvarez-Builla
Format: Article
Language:English
Published: MDPI AG 2012-07-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/17/8/8735
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author Juan José Vaquero
Antonio Cosme
Andres Molina
José Luis Novella
Maria Paz Matía
Rosa M. Suárez
Julio Alvarez-Builla
author_facet Juan José Vaquero
Antonio Cosme
Andres Molina
José Luis Novella
Maria Paz Matía
Rosa M. Suárez
Julio Alvarez-Builla
author_sort Juan José Vaquero
collection DOAJ
description The synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, a minor impurity of acyclovir, is described.<em> </em>Starting with commercial <em>N</em>-(9-acetyl-6-oxo-1<em>H</em>-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.
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spelling doaj.art-289694840f5243f985b01445ca197ab62022-12-21T18:22:43ZengMDPI AGMolecules1420-30492012-07-011788735874110.3390/molecules17088735Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of AcyclovirJuan José VaqueroAntonio CosmeAndres MolinaJosé Luis NovellaMaria Paz MatíaRosa M. SuárezJulio Alvarez-BuillaThe synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, a minor impurity of acyclovir, is described.<em> </em>Starting with commercial <em>N</em>-(9-acetyl-6-oxo-1<em>H</em>-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.http://www.mdpi.com/1420-3049/17/8/8735nucleosidesacyclovirdrug impuritiesphase transfer catalysis
spellingShingle Juan José Vaquero
Antonio Cosme
Andres Molina
José Luis Novella
Maria Paz Matía
Rosa M. Suárez
Julio Alvarez-Builla
Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir
Molecules
nucleosides
acyclovir
drug impurities
phase transfer catalysis
title Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir
title_full Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir
title_fullStr Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir
title_full_unstemmed Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir
title_short Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6<em>H</em>-purin-6-one, an Impurity of Acyclovir
title_sort synthesis of 9 9 1 2 ethanediylbis oxymethylene bis 2 amino 1 9 dihydro 6 lt em gt h lt em gt purin 6 one an impurity of acyclovir
topic nucleosides
acyclovir
drug impurities
phase transfer catalysis
url http://www.mdpi.com/1420-3049/17/8/8735
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