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Molecules 2012, 17(8), 8735-8741; doi:10.3390/molecules17088735
Article

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

1, 1, 1, 2, 2, 3 and 3,*
1 Fine Chemicals Pilot Plant Facility, University of Alcalá, 28871 Alcalá de Henares, Madrid, Spain 2 Department of Research and Development, Química Sintética S. A., c./Dulcinea s/n, 28805 Alcala de Henares, Madrid, Spain 3 Department of Organic Chemistry, University of Alcalá, 28871 Alcalá de Henares, Madrid, Spain
* Author to whom correspondence should be addressed.
Received: 16 June 2012 / Revised: 13 July 2012 / Accepted: 16 July 2012 / Published: 25 July 2012
(This article belongs to the Section Organic Synthesis)
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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.
Keywords: nucleosides; acyclovir; drug impurities; phase transfer catalysis nucleosides; acyclovir; drug impurities; phase transfer catalysis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Suárez, R.M.; Matía, M.P.; Novella, J.L.; Molina, A.; Cosme, A.; Vaquero, J.J.; Alvarez-Builla, J. Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, an Impurity of Acyclovir. Molecules 2012, 17, 8735-8741.

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