Piperazine → 1-Methyl-4-(1-piperazinyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 2230098Notes

Reaction equation

HRID 2230098 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:11])[N:9]=[CH:10][C:3]=12.OC1N=CN=C2N(C)N=CC=12.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(O)(C)C>[CH3:11][N:8]1[C:4]2=[N:5][CH:6]=[N:7][C:2]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[C:3]2[CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 2197514-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidineHCID 178481767HCID 178481767, compound

Product 1

HCID 113564151-Methyl-4-(1-piperazinyl)-1H-pyrazolo[3,4-d]pyrimidineYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

According to the method described in J. Org. Chem., 21: 1240-1256 (1956), 4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine was derived from 4-hydroxy-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (1.20 g, 8.03 mmol). To this partially purified product, an isopropanol solution (50 mL) of piperazine (5.55 g, 64.4 mmol) was added, followed by stirring at room temperature for 1 hour and then heating under reflux for 1 hour. 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 (1.44 g, 6.61 mmol).

Workup

  1. temperatureheating
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction solution was concentrated
  4. additionsaturated brine was added
  5. extractionthe mixture was extracted with chloroform
  6. washthe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ce9e58261ca84e85951547e0d8d23109
Source dataset
uspto-grants-2002_07
Patent number
US06423716B1

Reaction notes

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