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

HRID 1809709Notes

Reaction equation

HRID 1809709 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]=1

Participants

4

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 86667959HCID 86667959, compound

Product 1

HCID 86667964[3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-piperidin-1-yl-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

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%).

Workup

  1. temperatureat reflux for 16 hours
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography (a silica gel, MeOH

Sources & evidence

ORD record
ord-65cb55ea2d544e1da1326c58ec505170
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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