Dimethyl Sulfate → HCID 178469941, compound

HRID 2279621Notes

Reaction equation

HRID 2279621 reaction equation
C([N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]([OH:14])=[N:5]1)(=O)C.[C:15](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CN(C=O)C>[CH3:15][O:14][C:6]1[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:8][NH:4][N:5]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178469792HCID 178469792, compound

Product 1

HCID 178469941HCID 178469941, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of ethyl 1-acetyl-3-hydroxy-1H-pyrazole-4-carboxylate (2.1 g, 10.6 mmol) and potassium carbonate (1.5 g, 10.6 mmol) in 45 mL of DMF is stirred at RT for 30 minutes. Dimethyl sulfate (1.0 mL, 10.6 mmol) in 25 mL of DMF is then added dropwise over 10 min, and the resulting reaction mixture is heated to 70° C. for 4 h. The solvent is evaporated in vacuo, and the residue is dissolved in water and extracted with CH2Cl2 (2×30 mL). The combined organic extracts are dried (Na2SO4), filtered, and evaporated in vacuo to give a yellow/brown oil. Purification by silica gel column chromatography (gradient from 50% EtOAc/hexane to 80% EtOAc/hexane) affords the title compound as a clear, viscous oil which slowly solidifies on standing.

Workup

  1. customthe resulting reaction mixture
  2. temperatureis heated to 70° C. for 4 h
  3. customThe solvent is evaporated in vacuo
  4. dissolutionthe residue is dissolved in water
  5. extractionextracted with CH2Cl2 (2×30 mL)
  6. dry with materialThe combined organic extracts are dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give a yellow/brown oil
  10. customPurification by silica gel column chromatography (gradient from 50% EtOAc/hexane to 80% EtOAc/hexane)

Sources & evidence

ORD record
ord-e784e666dafc4d29853e1e1395ff898e
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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