5-FLUORO-1,3-DIMETHYLURACIL

Uses

5-Fluoro-1,3-dimethyluracil may be used as starting material in the following processes:

• Regioselective synthesis of tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones.
• To synthesize 5-bis(ethoxycarbonyl)methyl-1,3-dimethyluracil.
• To synthesize new highly conjugated propenylidene derivatives via aromatic Paterno-Buchi type cycloaddition with 1-methoxynaphthalene.

Synthesis Reference(s)

Tetrahedron, 46, p. 3093, 1990 DOI: 10.1016/S0040-4020(01)88400-3

General Description

Oxidation of 5-fluoro-1,3-dimethyluracil (5-FDMU) with m-chloroperbenzoic acid has been described. It is reported as antineoplastic drug. On photoirradiation, 5-fluoro-1,3-dimethyluracil yields the trans-anti cyclobutane dimer and the cis-syn cyclobutane dimer. UV irradiation of 5-FDMU and naphthalene in a protic medium affords 5-(1-naphthyl)uracil, while in aprotic media it undergoes stereoselective 1,4-cycloaddition reaction to give a barrelene derivative. The thermochemical parameters of 5-FDMU has been determined. It reacts with substituted benzenes in the presence of trifluoroacetic acid to generate 5-aryl-1,3-dimethyluracils via photosubstitution.