Cl.[F:2][C:3]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH3:12][CH2:13]N(C(C)C)C(C)C.[Br:21][C:22]1[CH:23]=[N:24][C:25](Cl)=[N:26][CH:27]=1.CCCCCC>CCO>[Br:21][C:22]1[CH:23]=[N:24][C:25]([N:6]2[CH2:7][CH2:8][C:3]([F:2])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:5]2)=[N:26][CH:27]=1
To a solution of 4-fluoropiperidine-4-carboxylate hydrochloride (0.70 g, 4.34 mmol) in EtOH (10.0 mL) was added DIPEA (1.92 mL, 10.86 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.70 g, 3.62 mmol). The reaction was then heated up to 70° C. for 1 h. After completion of reaction (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 3.0% EtOAc:hexane to obtain the desired product as a yellow solid (0.50 g, 42% yield). MS: 332.12 [M+H]+.
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