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Abstract
An improved synthesis of 9-benzyladenine (I), a model for a variety of biologically and therapeutically significant adenine nucleosides, has been reported. The target compound was synthesized by condensation of 1-benzyl-4-cyano-5-methoxymethyleneimino-imidazole (14) with guanidine. Compound 14 was prepared from 5-amino-1-benzyl-4-cyanoimidazole (5), which in turn was prepared by reaction of benzylamine with ethyl (Z)-N-(2-amino-1,2-dicyanovinyl) formimidate (13). The latter was synthesized by reaction of diaminomaleonitrile (6) with triethyl orthoformate.
ACKNOWLEDGMENTS
This research was supported by a grant (# RO1 CA 71079) from the National Institutes of Health. FAB mass spectral data were obtained from the Michigan State University Mass Spectral Facility, which is supported, in part, by a grant (P41RR-00480-0053) from the Biotechnology Research Technology Program, National Center for Research Resources, National Institutes of Health.