Triethylamine → Ethyl 4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenylcarbamate

HRID 915961Notes

Reaction equation

HRID 915961 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:24])[C:11]3[C:16]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][N:14]([CH3:23])[C:12]=3[N:13]=2)=[C:4]([O:25][CH3:26])[CH:3]=1.[C:27](Cl)(=[O:31])[O:28][CH2:29][CH3:30].C(N(CC)CC)C.[OH-].[Na+]>N1C=CC=CC=1.O1CCCC1>[CH:17]1([C:16]2[C:11]3[C:10](=[O:24])[NH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:27](=[O:31])[O:28][CH2:29][CH3:30])=[CH:3][C:4]=4[O:25][CH3:26])=[N:13][C:12]=3[N:14]([CH3:23])[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformate2×HCID 14798Sodium HydroxideHCID 1359488876-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 136005767Ethyl 4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenylcarbamateYield 57%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 6 ml tetrahydrofuran suspension of 100 mg (0.283 mmol) of the compound obtained in Example 44, 48 μl (0.50 mmol) of ethyl chlorocarbonate and 98 μl (0.707 mmol) of triethylamine were added, and the mixture was stirred at room temperature for 3 hours. Further, 48 μl (0.50 mmol) of ethyl chlorocarbonate and 1 ml of pyridine were added, and the mixture was stirred at room temperature for 18 hours. Then, a 1M aqueous solution of sodium hydroxide 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. 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/hexane=1/1˜2/1) to obtain 68 mg (57%) of the captioned compound.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1˜2/1)

Sources & evidence

ORD record
ord-ff4098e35ab540a6a0867cbaf03f9073
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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