Methyl iodide → HCID 66989093, compound

HRID 2407820Notes

Reaction equation

HRID 2407820 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([C:10]([OH:12])=[O:11])[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=1)[CH3:2].[C:16](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH2:1]([O:3][C:4]1[N:9]=[C:8]([C:10]([O:12][CH3:16])=[O:11])[C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66990671HCID 66990671, compound

Product 1

HCID 66989093HCID 66989093, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the compound prepared in Example 424 (1.8 g) in N,N-dimethylformamide (25 mL) was treated with potassium carbonate (1.76 g), followed by iodomethane (2.65 mL). The mixture was stirred at room temperature overnight. The solvent was concentrated in vacuo and the residue diluted with water, crude precipitated solids were collected by filtration, 2.14 g. These solids were taken in dichloromethane and purified by column chromatography on silica gel (5-25% ethyl acetate in hexanes) to provide the title compound (1.16 g) having the following physical data.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. additionthe residue diluted with water, crude
  3. customprecipitated solids
  4. filtrationwere collected by filtration, 2.14 g
  5. custompurified by column chromatography on silica gel (5-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c33f471877f84740b0af7d9136ae80c7
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…