Phenol → HCID 70873494, compound

HRID 925414Notes

Reaction equation

HRID 925414 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12](S(C)(=O)=O)[N:11]=2)=[CH:8][C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:11]=2)=[CH:8][C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 70873284HCID 70873284, compound

Product 1

HCID 70873494HCID 70873494, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.142 mmol) of ethyl 1-tert-butyl-5-[2-(methylsulfonyl)pyrimidin-4-yl]-1H-pyrazole-3-carboxylate were dissolved in 1.5 mL of dry DMF, 14.7 mg (0.156 mmol) of phenol and 59 mg (0.426 mmol) of potassium carbonate were added. The final suspension was stirred at 70° C. for 3 h then partitioned between H2O and AcOEt. The organic layer was washed with brine dried over Na2SO4, filtered and concentrated under reduced pressure to provide the title compound (77%).

Workup

  1. customthen partitioned between H2O and AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-62bf53a5b3964a3fbc157fdbfee794da
Source dataset
uspto-grants-2016_03
Patent number
US09284298B2

Reaction notes

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