The preparation of 5-cyanouracil and 5-cyano-2′-deoxyuridine from the corresponding 5-iodo derivative and cuprous cyanide

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Abstract
5-Cycnouracil has been prepared in high yield from cuprous cyanide and 5-Iodouracil. The daoxynucieoside has been similarly prepared from 5-iodo-2′-deoxy-uridine and this has anabled these campounds to be labelled with [14C] cyanide. Attempts have been made to incorporafs 5-cyanouracil into Escherichia coli 15T– and into Mycoplasma mycoides var. capri DNA under conditions in which several other 5-Substituted uracils have been incorporated, but without success. Similarly 5-cyano-2'-deoxyaridine could not be incorporated into the DNA of T3 phage under conditions in which 5-bromo-2'-deoxyuridine is easily incorporated. These results suggest that the criteria for a 5-substituted uracil to be incorporated into DNA in vivo depends on some factor other than the size of the substituent.