Journal of Medicinal Chemistry p. 572 - 574 (1980)
Update date:2022-08-17
Topics:
Barrio
Bryant
Keyser
Alkylation of 2-chloro-6-iodopurine with iodomethyl [(trimethylsilyl)oxy]ethyl ether at -63°C and subsequent treatment of the 9-substituted chloroiodopurine with K2CO3 in aqueous dioxane at 25°C and then with NH3 under pressure at 150°C provided 9-[(2-hydroxyethoxy)methyl]guanine (1a), a potent antiviral agent against Herpes simplex virus type 1, in excellent yield. Its monophosphate (1g), which is enzymatically produced from 1a in the virus-infected cell, was also synthesized. 6-Chloropurine and 4-(methylthio)pyrimidin-2-one anions were similarly alkylated with iodomethyl [(trimethylsilyl)oxy]ethyl ether, and the products were transformed by treatment with methanolic NH3 at 110°C into 9-[(2-hydroxyethoxy)methyl]adenine and 1-[(2-hydroxyethoxy)methyl]cytosine respectively. The synthesis of these analogues, heretofore difficult to prepare by a simple procedure, has been conveniently accomplished.
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