1-(4-Nitrophenyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine → 1-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

HRID 655837

Reaction equation

HRID 655837 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3=[N:15][CH:16]=[N:17][C:18]([NH2:19])=[C:13]3[CH:12]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3=[N:15][CH:16]=[N:17][C:18]([NH2:19])=[C:13]3[CH:12]=[N:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 2210751-(4-Nitrophenyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Title compound 10A, 1-(4-nitro-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (1.0 g, 3.9 mmol) was added to 10% w/w palladium on carbon (0.1 g, 10% w/w) suspended in ethanol (300 ml). This was stirred for 42 hours at room temperature under an atmosphere of hydrogen. The reaction mixture was filtered to remove the palladium residues and the filtrate was concentrated to dryness in vacuo. The resultant residue was purified by column chromatography using DCM/MeOH (96:4) as eluent to yield the title compound as an off-white solid. (0.53 g, 2.3 mmol, 60%). LCMS: [M+H]+=227, Rt=0.64 min, 100% purity.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the palladium residues
  3. concentrationthe filtrate was concentrated to dryness in vacuo
  4. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-3d56aac5c1494b83bbf004dc23b2879e
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Linked notes

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