Morpholine → (5'-Isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine

Participants

Reaction Conditions

Reaction Steps

(5-Bromo-pyrimidin-2-yl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amine (3.30 g) is dissolved in toluene (30 ml), and thereto are added tris(dibenzylideneacetone)dipalladium (1.26 g), 2-(di-tert-butylphosphino)biphenyl (1.23 g), morpholine (2.4 ml) and sodium tert-butoxide (1.32 g) and the mixture is degassed under reduced pressure and stirred under nitrogen flow at 50° C. overnight. To the reaction mixture is added a saturated brine, and 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 silica gel column chromatography (hexane:ethyl acetate=19:1→3:1) to give (5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amine (1.11 g). MS (m/z): 487 [M+H]+

Provenance & Evidence