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 897809Notes

Reaction equation

HRID 897809 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-b43a4708fb4c408fab405032372bfeb6
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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