Cesium carbonate → 3-(4-Tert-butylphenyl)-5,5-dimethyl-1-[(2-{[6-(pyrrolidin-1-yl-methyl)pyridin-3-yl]amino}pyridin-4-yl)methyl]imidazolidine-2,4-dione

Participants

Reaction Steps

To a solution of 0.5 g 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, 0.32 g of 5-bromo-2-(pyrrolidin-1-ylmethyl)pyridine obtained in stage a) below, 77 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (xantphos), 38 mg of palladium acetate and 1.75 g of caesium carbonate. The reaction mixture is refluxed for 7 hours and then filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol (87/13 by volume) to give 62 mg of 3-(4-tert-butylphenyl)-5,5-dimethyl-1-[(2-{[6-(pyrrolidin-1-yl-methyl)pyridin-3-yl]amino}pyridin-4-yl)methyl]imidazolidine-2,4-dione, the characteristics of which are as follows:

Provenance & Evidence