Catalytic amination of 5-iodouracil derivatives

Heterocyclic 5-amino uracil derivatives were prepared by catalytic amination of 1,3-dibenzyl-5-iodouracil using (CuOTf)2·PhH, 1,10-phenanthroline, dibenzylidene acetone, and Cs2CO3 as base in xylenes at 95°C. Imidazole and 2-amino thiazoline were problematic using the Cu catalyst, but were effectively coupled using Ni(COD)2, dppf, and NatOBu in toluene at 100°C. These are the first examples of catalytic amination with a uracil substrate.