The synthesis and polymerization of 5-hydroxymethyluracil acrylate and methacrylate

Abstract

Polymerizable derivatives of 5-hydroxymethyluracil were prepared using acrylic acid and methacrylic acid, and polymerizations were carried out. These derivatives may at some future time find applications as anticancer drugs and antiviral drugs with reduced side effects or as selective chromatographic plastics used in chromatography. The products prepared in the reactions were : 1) 5-hydroxymethyluracil acrylate and 2) 5-hydroxymethyluracil methacrylate. These products were slightly soluble in ethyl acetate. The assigned structures for the products are supported by infrared spectroscopy, nuclear magnetic resonance spectroscopy and elemental analysis.

The esterification of 5-hydroxymethyluracil with the two acids proceeded quite readily with excellent yields. The purification of the monomer was accomplished by selective absorption of impurities on silica gel in ethyl acetate solvent.

Polymerization of the acrylate and methacrylate monomers was achieved by the free radical polymerization initiator -azobisiso-butyronitrile (AIBN). The degree of polymerization seemed to be related to the time of polymerization. Viscosity studies were performed on the polymers using a Cannon-Fenske viscometer.