Methyl iodide → HCID 22281998, compound

HRID 1368667Notes

Reaction equation

HRID 1368667 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17].[C:18](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[CH3:18][O:8][C:4]1[C:3]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[C:2]([NH2:1])[N:6]([CH3:7])[N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22281996HCID 22281996, compound

Product 1

HCID 22281998HCID 22281998, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-4-(2-methoxyphenoxy)-1-methyl-1,2dihydro-3H-pyrazol-3-one (Preparation 69) (300 mg), caesium carbonate (1.25 g) and iodomethane (200 mg) in dry dimethylformamide (5 ml) was stirred under a nitrogen atmosphere for 24 hours at room temperature. The reaction mixture was partitioned between ethyl acetate (7×25 ml) and water (40 ml) and the combined organic extracts were dried (magnesium sulfate) and concentrated under vacuum. The residue was purified by chromatography on a Biotage Flash™ 40s silica cartridge (40 g silica) using neat ethyl acetate and then 1% methanol/dichloromethane as eluants to give the title compound as a brown solid (90 mg), Rf 0.57 (10% methanol/dichloromethane).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (7×25 ml) and water (40 ml)
  2. dry with materialthe combined organic extracts were dried (magnesium sulfate)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by chromatography on a Biotage Flash™ 40s silica cartridge (40 g silica)

Sources & evidence

ORD record
ord-22bdb1bbe4ae4662bdece57465cc84db
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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