Piperazine → 1-Phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 2230099

Reaction equation

HRID 2230099 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]2[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:15]=[CH:16][C:9]=12>C(O)(C)C>[C:17]1([N:14]2[C:10]3=[N:11][CH:12]=[N:13][C:8]([N:1]4[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]4)=[C:9]3[CH:16]=[N:15]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 2197524-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 8556141-Phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidineYield 88%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To an isopropanol solution (10 mL) of piperazine (3.74 g, 43.4 mmol), 4-chloro-1-phenylpyrazolo[3,4-d]pyrimidine (100 g, 4.34 mmol) described in J. Org. Chem., 21: 1240-1256 (1956) was added, followed by heating under reflux for 6 hours. The reaction solution was concentrated, saturated brine was added thereto, the mixture was extracted with chloroform, the extract was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated to give the target compound (1.07 g, 3.82 mmol).

Workup

  1. addition, 21: 1240-1256 (1956) was added
  2. temperatureby heating
  3. temperatureunder reflux for 6 hours
  4. concentrationThe reaction solution was concentrated
  5. additionsaturated brine was added
  6. extractionthe mixture was extracted with chloroform
  7. washthe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8a92fe3fcece4356bb472dc60d350135
Source dataset
uspto-grants-2002_07
Patent number
US06423716B1

Linked notes

Loading…