[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.I[C:12]1[C:13]([NH:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]2)=[N:14][C:15]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:16][C:17]=1[O:18][CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:19][O:18][C:17]1[N:16]=[C:15]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:14]=[C:13]([NH:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]2)[C:12]=1[C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=2[N:7]=1Following the same procedure as in step 3 of Example 337 using 5-methyl-1,3-benzothiazole (52.2 mg, 0.35 mmol, 1.80 equiv), tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (100.0 mg, 0.19 mmol, 1.00 equiv), cesium Carbonate (0.37 g, 6.00 equiv), Pd(PPh3)4 (40.4 mg, 0.03 mmol, 0.18 equiv) and copper (I) iodide (6.7 mg, 0.09 mmol, 0.18 equiv) in DMF (6 mL). The crude product was purified by chromatography on a silica gel column eluting with petroleum ether/ethyl acetate (15:1-3:1) to afford the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 541.
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