[CH3:1][N:2]([CH2:10]C1CCNCC1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl.Cl[C:19]1C=C[N:22]=[CH:21][N:20]=1.[CH3:25][CH2:26][N:27]([CH:31]([CH3:33])C)[CH:28]([CH3:30])C>CC(O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:10][N:2]([CH:1]1[CH2:25][CH2:26][N:27]([C:28]2[CH:30]=[CH:19][N:20]=[CH:21][N:22]=2)[CH2:31][CH2:33]1)[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8]tert-Butyl methyl(piperidin-4-ylmethyl)carbamate (4.67 mmol, 1.0 eq) and 4-chloropyrimidine hydrochloride (14.0 mmol, 3.0 eq) were dissolved in 2-propanol (18 ml) and DIPEA (23.33 mmol. 5.0 eq) and refluxed for 16 hours. After monitoring by TLC, the reaction solution was diluted with ethyl acetate and sat. sodium hydrogen carbonate solution, and the phases were separated. The aqueous phase was washed with ethyl acetate. The combined organic phases were washed 1× with sat. NaCl solution, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution). Yield: 78%
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