benzyl 4-[4-amino-3-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate → 3-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432519Notes

Reaction equation

HRID 432519 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:27]3[CH2:32][CH2:31][N:30](C(OCC4C=CC=CC=4)=O)[CH2:29][CH2:28]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][CH2:18][C:19]4[O:20][C:21]([CH3:24])=[CH:22][CH:23]=4)=[C:13]([O:25][CH3:26])[CH:12]=3)[C:3]=12>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:26][O:25][C:13]1[CH:12]=[C:11]([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][C:2]=3[NH2:1])[N:8]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[N:9]=2)[CH:16]=[CH:15][C:14]=1[NH:17][CH2:18][C:19]1[O:20][C:21]([CH3:24])=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 22346718benzyl 4-[4-amino-3-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate

Product 1

HCID 223470923-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 14.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl 4-[4-amino-3-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (0.18 g, 0.000317 mol) and 20% palladium hydroxide on carbon (0.02 g) in ethyl acetate (10 mL) was stirred under atmosphere of hydrogen at room temperature for 18 hours. The mixture was filtered and solvents were removed. The residue was purified by flash column chromatography on silica using 5%-10% methanol/dichloromethane (2% NH4OH) to give 3-(3-methoxy-4-{[(5-methyl-2-furyl)methyl]amino}phenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.02 g, 0.000046 mol).

Workup

  1. filtrationThe mixture was filtered
  2. customsolvents were removed
  3. customThe residue was purified by flash column chromatography on silica using 5%-10% methanol/dichloromethane (2% NH4OH)

Sources & evidence

ORD record
ord-b9c5885921634983ab6628ddeb061a00
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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