[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([NH2:31])=[O:30])[CH:9]=2)[C:5](I)=[CH:4][N:3]=1.[C:33]([C:35]1[CH:40]=[CH:39][C:38]([C:41]([N:43]2[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]2)=[O:42])=[CH:37][CH:36]=1)#[CH:34]>C(#N)C.[Cu](I)I.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>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([NH2:31])=[O:30])[CH:9]=2)[C:5]([C:34]#[C:33][C:35]2[CH:36]=[CH:37][C:38]([C:41]([N:43]3[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]3)=[O:42])=[CH:39][CH:40]=2)=[CH:4][N:3]=1To a degassed solution of 5-(2-amino-5-iodopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (140 mg, 0.24 mmol), (4-ethynylphenyl)(4-methylpiperazin-1-yl)methanone (98 mg, 0.43 mmol) and TEA (0.335 mL, 2.4 mmol) in dry ACN (2.5 mL) were added copper iodide (2.5 mg, 0.012 mmol) and Pd(PPh3)2Cl2 (8.4 mg, 0.012 mmol). The mixture was heated at 80° C. for 2 h, then the solvent was evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH/7N NH3 in MeOH 95/4/1) to afford the title compound (131 mg, 80%).
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