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Starting from uridine, 1-beta-D-arabinofluranosyl-5-hydroxymethyl-N4-alkylcytosines were prepared via 1-beta-D-arabinofuranosyluracil. During the course of this synthetic work, an interesting observation has been made that 5-acetoxy group of 1-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)-5-acetoxymethyluracil and its derivatives was easily displaced at room temperature with alkylamine in methanol, but not in chloroform, to give the corresponding 5-alkylaminomethyl derivatives.
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