Methyl iodide → HCID 86678199, compound

HRID 1747545Notes

Reaction equation

HRID 1747545 reaction equation
[CH2:1]([O:3][CH:4]([O:16][CH2:17][CH3:18])[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]=[N:13][NH:14][CH:15]=2)=[N:9][CH:10]=1)[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].IC>C(#N)C>[CH2:17]([O:16][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:15]=[N:14][N:13]([CH3:19])[N:12]=2)=[N:9][CH:10]=1)[CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178470857HCID 178470857, compound

Product 1

HCID 86678199HCID 86678199, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile (25 mL) was dissolved 5-(diethoxymethyl)-2-(1H-1,2,3-triazol-4-yl) pyridine (1.34 g, 5.40 mmol) obtained in Step 4. To the solution were added potassium carbonate (2.24 g, 5.40 mmol) and iodomethane (0.405 mL, 6.48 mmol) and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure and water was added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give 5-(diethoxymethyl)-2-(2-methyl-2H-1,2,3-triazol-4-yl)pyridine (698 mg, 49% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added
  3. extractionExtraction with ethyl acetate
  4. washwashing with saturated brine
  5. dry with materialdrying over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent in the filtrate was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-78df27123c7549e4b636c90d01f62499
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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