Methyl iodide → Methyl 1,4-dimethyl-1H-pyrazole-5-carboxylate

HRID 244615Notes

Reaction equation

HRID 244615 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[C:11](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C.O.C(Cl)Cl>[CH3:11][N:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([CH3:1])[CH:3]=[N:4]1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 3467807Methyl 4-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 20718564Methyl 1,4-dimethyl-1H-pyrazole-5-carboxylateYield 31.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 4-methyl-1H-pyrazole-5-carboxylate (0.5 g) and cesium carbonate (1.16 g) were dissolved in acetonitrile (10 ml). Methyl iodide (0.25 ml) was added and the mixture stirred at RT for 16 h. The reaction mixture was diluted with water (20 ml) and DCM (20 ml) and separated using a hydrophobic frit. The aqueous layer was extracted with DCM (2×20 ml) using a hydrophobic frit. The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound (0.172 g) as a colourless oil.

Workup

  1. customseparated
  2. extractionThe aqueous layer was extracted with DCM (2×20 ml)
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography
  5. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-366bb9393deb4a7ebef3a57a10006196
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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