[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[CH:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[C:18]1[C:19]([NH:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[N:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1.C(N(CC)CC)C.[Cl-].[NH4+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:29][C:28]([CH3:31])([CH3:30])[CH2:27][NH:26][C:19]1[C:18]([C:16]#[C:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:9][CH:10]=2)=[CH:23][N:22]=[C:21]([C:24]#[N:25])[N:20]=1To a solution of 1-methyl-4-(4-prop-2-ynyl-phenyl)-piperazine (0.75 mmol) and 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (0.5 mmol) in THF (7 ml), triethylamine (1.5 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.025 mmol) and copper (I) iodide (0.05 mmol) are added. The reaction mixture is heated at 60° C. c for 3 h. Saturated aqueous solution of ammonium chloride is added to the reaction mixture and then aqueous layer is extracted with two 50 ml portions of AcOEt. The combined extracts are washed with brine, dried over sodium sulfate and concentrated under vacuum to give crude product which is purified by reverse phase HPLC. Yield: 25%. Rf=0.5 (MeOH:CH2Cl2=5:95)
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