Cl.[C:2]([C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#[N:3].CCN(C(C)C)C(C)C.[Br:24][C:25]1[CH:26]=[N:27][C:28](Cl)=[N:29][CH:30]=1.CCCCCC>CCO>[Br:24][C:25]1[CH:26]=[N:27][C:28]([N:7]2[CH2:8][CH2:9][C:4]([C:2]#[N:3])([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:5][CH2:6]2)=[N:29][CH:30]=1
To a solution of ethyl 4-cyanopiperidine-4-carboxylate hydrochloride (0.56 g, 2.6 mmol) in EtOH (10 mL) was added DIPEA (0.8 mL, 4.29 mmol) at rt and stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.33 g, 1.73 mmol). The reaction mixture was 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 10% EtOAc:hexane to obtain the product as a yellow solid (0.4 g, 68% yield). 1H NMR (DMSO-d6): δ 1.20 (t, J=7.20 Hz, 3H), 2.04 (m, 2H), 2.22 (m, 2H), 3.22 (m, 2H), 4.15 (q, J=7.20 Hz, 2H), 4.32 (m, 2H) and 8.50 (s, 2H).
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