Cl[C:2]1[N:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:3]=1.[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:30]([O:29][C:27]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:2]2[N:3]=[C:4]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:5]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[N:7]=2)[CH2:22][CH2:23]1)=[O:28])([CH3:33])([CH3:31])[CH3:32]To a mixture of 2-[2-chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol (500 mg, 1.68 mmol), 4-amino-1-Boc-piperidine (404 mg, 2.02 mmol), sodium tert-butoxide (243 mg, 2.52 mmol) in dioxane (2.5 mL) was added under an argon atmosphere palladium(II) acetate (30 mg, 0.14 mmol) and 2-(dicyclohexylphosphino)biphenyl (94 mg, 0.27 mmol) and the reaction mixture was heated to 150° C. for 30 minutes in a microwave oven. It was diluted with ethyl acetate (15 mL) and washed with water (15 mL) and brine (15 mL). The aqueous layers were extracted with ethyl acetate (15 mL) and dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 60:40) afforded the title compound (230 mg, 30%) as a light brown oil.
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