Cesium carbonate → 3-(4-Tert-butylphenyl)-5,5-dimethyl-1-{[2-(pyrimidin-5-ylamino)pyridin-4-yl]methyl}imidazolidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 200 mg of 1-[(2-aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione hydrochloride obtained in stage c) below in 5 mL of dioxane are successively added under argon 11.1 mg of palladium diacetate, 29 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)(Xantphos), 777 mg of caesium carbonate and 86.8 mg of 5-bromopyrimidine. The reaction mixture is heated at 100° C. for 5 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, methanol and concentrated aqueous ammonia (95/4/1 by volume) to give 135 mg of 3-(4-tert-butylphenyl)-5,5-dimethyl-1-{[2-(pyrimidin-5-ylamino)pyridin-4-yl]methyl}imidazolidine-2,4-dione in the form of an off-white solid, the characteristics of which are as follows:

Provenance & Evidence