Methyl iodide → HCID 67653887, compound

HRID 2393339Notes

Reaction equation

HRID 2393339 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([O:14][C:15]2[CH:16]=[N:17][N:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[CH:19]=2)[N:3]=1.[H-].[Na+].C(CNC[CH:34]=[O:35])=O.[CH3:36]I>CN(C)C=O.COCCOC>[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9](=[CH:36][O:35][CH3:34])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([O:14][C:15]2[CH:16]=[N:17][N:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[CH:19]=2)[N:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18975607HCID 18975607, compoundHCID 202686642,2'-Azanediyldiacetaldehyde

Product 1

HCID 67653887HCID 67653887, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
45 °C

Procedure

The intermediate methyl 2-[2,4-dimethyl-6-(1-(2-methylphenyl)-1H-pyrazol-4-yloxy)-pyrimidin-5-yl]-acetate (6.0 g, 17 mmol), sodium hydride (0.9 g, 37 mmol) and N,N-diformylmethylamine (6 ml) in a mixture of dimethylformamide (20 ml) and 1,2-dimethoxyethane (20 ml) is stirred at 45° C. for 3 hours. Methyliodide (4.2 g, 30 mmol) is added at room temperature and stirring is continued for additional 16 hours. Dilution with ether, washing with brine, drying and chromatography on silicagel (eluant ethyl acetate/hexane 3:7) gives methyl 2-[2,4-dimethyl-6-(1-(2-methylphenyl)-1H-pyrazole-4-yloxy)-pyrimidin-5-yl]-3-methoxyacrylate as a colorless oil.

Workup

  1. stirringstirring
  2. waitis continued for additional 16 hours
  3. washDilution with ether, washing with brine
  4. customdrying

Sources & evidence

ORD record
ord-4a4730f52f544326813c7b8d75189987
Source dataset
uspto-grants-1998_09
Patent number
US05807863

Reaction notes

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