N,N,N',N'-Tetramethylazodicarboxamide → 3-Cyclohexyl-6-[2-methoxy-4-(3-methyl-2-oxo-1-imidazolidinyl)phenyl]-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 915965Notes

Reaction equation

HRID 915965 reaction equation
O1CCCC1.[CH:6]1([C:12]2[C:20]3[C:19](=[O:21])[NH:18][C:17]([C:22]4[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:35])[N:30]([CH2:32][CH2:33]O)[CH3:31])=[CH:24][C:23]=4[O:36][CH3:37])=[N:16][C:15]=3[N:14]([CH3:38])[N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.N(C(N(C)C)=O)=NC(N(C)C)=O>O>[CH:6]1([C:12]2[C:20]3[C:19](=[O:21])[NH:18][C:17]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH2:33][CH2:32][N:30]([CH3:31])[C:29]5=[O:35])=[CH:24][C:23]=4[O:36][CH3:37])=[N:16][C:15]=3[N:14]([CH3:38])[N:13]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 8028TetrahydrofuranHCID 136005850N'-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]-N-(2-hydroxyethyl)-N-methylurea

Product 1

HCID 1360058363-Cyclohexyl-6-[2-methoxy-4-(3-methyl-2-oxo-1-imidazolidinyl)phenyl]-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 3 ml tetrahydrofuran suspension of 114 mg (0.25 mmol) of the compound obtained in Example 151, 52 mg (0.30 mmol) of 1,1′-azobis(N,N-dimethylformamide) and 75 μl (0.30 mmol) of n-tributylphosphine were added, and the mixture was stirred at room temperature for 20 hours. Then, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain 71.6 mg (66%) of the captioned compound.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-83b20b0145574b14a8e03e05e91d1b10
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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