Binap, (A+-)- → Tert-butyl 4-(2-{2-[(3,5-bis-trifluoromethyl-benzyl)-ethyl-amino]-5-trifluoromethyl-benzylamino}-pyrimidin-5-yloxy)-butyrate

Participants

Reaction Conditions

Reaction Steps

(2-Aminomethyl-4-trifluoromethyl-phenyl)-(3,5-bis-trifluoromethyl-benzyl)-ethyl-amine (165 mg) is dissolved in toluene (3 ml) and thereto are added tert-butyl 4-(2-chloro-pyrimidin-5-yloxy)-butyrate (202 mg), tris(dibenzylideneacetone)dipalladium(0) (68 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (92 mg) and sodium tert-butoxide (71 mg), and the mixture is stirred under nitrogen flow at 80° C. for 5 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=7:1) to give tert-butyl 4-(2-{2-[(3,5-bis-trifluoromethyl-benzyl)-ethyl-amino]-5-trifluoromethyl-benzylamino}-pyrimidin-5-yloxy)-butyrate (73 mg). MS (m/z): 681 [M+H]+

Provenance & Evidence