Hydrochloric Acid → (S)-N-methyl-N-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Reaction equation
[CH3:1][N:2]([C@H:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1)[C:3]1[N:8]=[CH:7][N:6]=[C:5]2[N:9](COCC[Si](C)(C)C)[N:10]=[CH:11][C:4]=12.Cl>CCO>[CH3:1][N:2]([C@H:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1)[C:3]1[N:8]=[CH:7][N:6]=[C:5]2[NH:9][N:10]=[CH:11][C:4]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of (S)—N-methyl-N-(piperidin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (310 mg, 0.85 mmol) in EtOH (7.5 mL), cone. HCl (2.5 mL) was added and the reaction mixture was heated at 60° C. for 5 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in MeOH (5 mL) and a polymer support carbonate resin was added until the mixture turned basic (Checked by litmus paper). The reaction mixture was filtered and the filtrate was concentrated in vacuo to yield the titled intermediate (189 mg, 95%), which was used further without further purification. LC-MS: m/z [M+1]=233.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutionthe residue was dissolved in MeOH (5 mL)
- additiona polymer support carbonate resin was added until the mixture
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-eb2a273a7a8b4b1ca8700bcbe185b0bc
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273028B2
Reaction notes
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