Purine acyclic nucleosides. Unambiguous synthesis of acyclovir via a furazano[3,4-d]pyrimidine |
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Authors: | James L. Kelley Howard J. Schaeffer |
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Abstract: | Acyclovir was synthesized in five steps from 7-formamido-5-methylthiofurazano[3,4-d]pyrimidine 2 . Alkylation of 2 with 2-(benzoyloxy)ethoxymethyl chloride, followed by reductive cleavage of the furazan ring gave 9-[[2-(benzoyloxy)ethoxy]methyl]-2-(methylthio)adenine 5 . Hydrolysis of the 6-amino group of 5 , followed by amination of 7 with ammonia gave 9-[(2-hydroxyethoxy)methyl]guanine ( 1 , acyclovir). |
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