Morpholine → Ethyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate

Participants

Reaction Conditions

Reaction Steps

Ethyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate (614 mg) is dissolved in toluene (6.5 ml), and thereto are added tris(dibenzylideneacetone)dipalladium(0) (87 mg), 2-(di-tert-butylphosphino)biphenyl (114 mg), morpholine (166 μl) and sodium tert-butoxide (183 mg) and the mixture is stirred under nitrogen flow at 60° C. for 2 hours. To the reaction mixture is added a saturated brine, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (hexane:ethyl acetate=9:1→4:1) to give ethyl (2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-carbamate (476 mg). MS (m/z): 652 [M+H]+

Provenance & Evidence