1-Methylpiperazine → 1-Cyclohexyl-5-{2-methoxy-4-[(4-methyl-1-piperazinyl)methyl]phenyl}-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 915983Notes

Reaction equation

HRID 915983 reaction equation
[CH:1]1([N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=4[O:25][CH3:26])=[N:11][C:10]=3[C:9]([CH3:27])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.ClCCCl>[CH:1]1([N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:24]=[CH:23][C:20]([CH2:21][N:32]5[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]5)=[CH:19][C:18]=4[O:25][CH3:26])=[N:11][C:10]=3[C:9]([CH3:27])=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 136005822HCID 136005822, compound

Product 1

HCID 1360058811-Cyclohexyl-5-{2-methoxy-4-[(4-methyl-1-piperazinyl)methyl]phenyl}-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 76.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a 2 ml 1,2-dichloroethane solution of 61 mg (0.166 mmol) of the compound obtained in Example 233, 37 μl (0.332 mmol) of N-methylpiperazine, 10 μl of acetic acid, and 53 mg (0.252 mmol) of sodium triacetoxyborohydride were added, and the mixture was stirred at room temperature for 1 hour. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, whereafter the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol=10/1) to obtain 57 mg (76%) of the captioned compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, whereafter the solvent
  4. distillationwas distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-9b8f2f26014d4e33be512e7811e9df2c
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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