Methanol → HCID 57562648, compound

HRID 1725474Notes

Reaction equation

HRID 1725474 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[CH:12][N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:10]=2)[CH:5]=[N:4][CH:3]=1.[C:22](=[O:25])([O-])[OH:23].[Na+].[CH3:27]O.[C]=O>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[CH3:19][Si:18]([CH3:21])([CH3:20])[CH2:17][CH2:16][O:15][CH2:14][N:11]1[CH:12]=[CH:13][C:9]([NH:8][C:6]2[N:7]=[C:2]([C:22]([O:23][CH3:27])=[O:25])[CH:3]=[N:4][CH:5]=2)=[N:10]1

Participants

8

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 57562642HCID 57562642, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 57562648HCID 57562648, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.41 g of 6-chloro-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)pyrazin-2-amine, 320 mg of palladium acetate, 790 mg of 11′-bisdiphenylphosphinoferrocene, 890 mg of sodium hydrogen carbonate, 10 ml of methanol and 10 ml of N,N-dimethylformamide was stirred at 100° C. for 15 hours under 3 atmospheric pressure of carbon monoxide, cooled to room temperature, and then diluted with ethyl acetate. An insoluble matter was filtered off using Celite and the resulting ethyl acetate solution was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1 to 1/1) to give the title compound.

Workup

  1. filtrationAn insoluble matter was filtered off
  2. washthe resulting ethyl acetate solution was washed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1 to 1/1)

Sources & evidence

ORD record
ord-b50c668c034a4b3785d2386abfdec66f
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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