N-(2-Aminoethyl)piperidine → [3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-piperidin-1-yl-ethyl)-amine
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][C:13](Cl)=[N:14][CH:15]=3)[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[N:26]1([CH2:32][CH2:33][NH2:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CC(O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][C:13]([NH:34][CH2:33][CH2:32][N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:14][CH:15]=3)[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:9]=2)[CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
A mixture of 3-(6-bromo-pyridin-2-yl)-6-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine (from Example 31 supra) (1.0 g, 2.3 mmol), 2-(piperidin-1-yl)ethanamine (324 mg, 2.53 mmol) and TEA (256 mg, 2.53 mmol) in IPA (30 mL) was stirred at reflux for 16 hours. After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by column chromatography (a silica gel, MeOH:dichloromethane, 1:100) to give [3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-piperidin-1-yl-ethyl)-amine as a white solid. (Yield 285 mg, 23.3%).