Methyl iodide → HCID 66958961, compound

HRID 1984513Notes

Reaction equation

HRID 1984513 reaction equation
[C:1]([C:3]([CH3:19])([CH3:18])[CH2:4][C:5]1[N:9]([CH2:10][CH2:11][OH:12])[N:8]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=1)#[N:2].I[CH3:21].[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[C:1]([C:3]([CH3:18])([CH3:19])[CH2:4][C:5]1[N:9]([CH2:10][CH2:11][O:12][CH3:21])[N:8]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=1)#[N:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66959203HCID 66959203, compound

Product 1

HCID 66958961HCID 66958961, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-(2-cyano-2-methylpropyl)-1-(2-hydroxyethyl)-1H-pyrazole-3-carboxylate (6.12 g, 23.1 mmol) in THF (50 mL) was cooled to approximately 0° C. under nitrogen, and iodomethane (3.28 g, 23.1 mmol) was added. Sodium hydride (0.924 g of 60% in mineral oil, 23.1 mmol) was added in one portion. The mixture was allowed to warm to room temperature slowly and stirred overnight. Saturated aqueous ammonium chloride was added, and the mixture was extracted three times with tert-butyl methyl ether. The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a yellow oil. The oil was purified by chromatography on a HORIZON HPFC system (65I cartridge, eluting with ethyl acetate) to provide 3.68 g of ethyl 5-(2-cyano-2-methylpropyl)-1-(2-methoxyethyl)-1H-pyrazole-3-carboxylate as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted three times with tert-butyl methyl ether
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto provide a yellow oil
  6. customThe oil was purified by chromatography on a HORIZON HPFC system (65I cartridge, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-6e69166cf8164c7b8a7cab0ee7badf09
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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