HCID 178437860, compound → HCID 178437861, compound

HRID 487259Notes

Reaction equation

HRID 487259 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=[CH:18][CH:17]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:26][CH3:27])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pt]=O.C(O)(=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([CH:16]4[CH:25]5[CH:20]([CH2:21][CH2:22][CH2:23][CH2:24]5)[NH:19][CH2:18][CH2:17]4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:26][CH3:27])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 178437860HCID 178437860, compound

Product 1

HCID 178437861HCID 178437861, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

1-Cyclopentyl-3-ethyl-6-(4-quinolinyl)-pyrazolo[3,4-d]-pyrimidin-4-one (1.0 g, 2.7 mmol), platinum oxide (0.15 g) and acetic acid (50 ml) were combined and placed in a parr hydrogenator at 42 psi. The reaction mixture was heated at about 70° C. by an external heating jacket for 6 hours. The reaction mixture was cooled to room temperature, the catalyst was removed by filtration through a celite pad and the pad was washed with ethanol. Concentrated HCl (3 ml) was added to the filtrate and the solvents were removed in vacuo. The residue was dissolved in isopropanol (10 ml) and was heated on a steam bath for 10 minutes. A solid was collected by filtration, washed with isopropanol and dried at 90° C. in high vacuum to afford 0.83 g (84%) of 1-cyclopentyl-3-ethyl-6-(perhydro-4-quinolinyl)pyrazolo[3,4-d]pyrimidin-4-one as a white powder, m.p. >300° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe catalyst was removed by filtration through a celite pad
  3. washthe pad was washed with ethanol
  4. additionConcentrated HCl (3 ml) was added to the filtrate
  5. customthe solvents were removed in vacuo
  6. dissolutionThe residue was dissolved in isopropanol (10 ml)
  7. temperaturewas heated on a steam bath for 10 minutes
  8. filtrationA solid was collected by filtration
  9. washwashed with isopropanol
  10. customdried at 90° C. in high vacuum

Sources & evidence

ORD record
ord-3daa45fed8304ec1b84c0555f98ab3d7
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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