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

doi:10.3390/molecules17088735

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

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

Rosa M. Suárez¹, Maria Paz Matía¹, José Luis Novella¹, Andres Molina², Antonio Cosme², Juan José Vaquero³ and Julio Alvarez-Builla^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; in revised form: 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

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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.

AMA Style

Suárez RM, Matía MP, Novella JL, Molina A, Cosme A, Vaquero JJ, 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(8):8735-8741.

Chicago/Turabian Style

Suárez, Rosa M.; Matía, Maria Paz; Novella, José Luis; Molina, Andres; Cosme, Antonio; Vaquero, Juan José; Alvarez-Builla, Julio. 2012. "Synthesis of 9,9′-[1,2-Ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, an Impurity of Acyclovir." Molecules 17, no. 8: 8735-8741.

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