Cesium carbonate → 3-(4-Tert-butylphenyl)-5,5-dimethyl-1-[2-(5-pyrrolidin-1-ylmethylpyridin-3-ylamino)pyridin-4-ylmethyl]imidazolidine-2,4-dione

Participants

Reaction Steps

To a solution of 500 mg of 1-[(2-aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione obtained in stage c) of Example 7 in 15 mL of dioxane are successively added, under argon, 46 mg of palladium diacetate, 95 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)(Xantphos), 1.8 g of caesium carbonate and 0.39 g of 3-Bromo-5-pyrrolidin-1-ylmethylpyridine obtained in stage a) below. The reaction mixture is refluxed for 4 hours and then filtered, and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol (96/4 by volume) to give 90 mg of 3-(4-tert-butylphenyl)-5,5-dimethyl-1-[2-(5-pyrrolidin-1-ylmethylpyridin-3-ylamino)pyridin-4-ylmethyl]imidazolidine-2,4-dione, the characteristics of which are as follows:

Provenance & Evidence