Sodium hydride → 5,5-Dimethyl-1-(2-ethylpyrid-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione

HRID 899976Notes

Reaction equation

HRID 899976 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:22])[NH:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[C:5]1=[O:21].[CH2:23]([C:25]1[CH:30]=[C:29]([CH2:31]Br)[CH:28]=[CH:27][N:26]=1)[CH3:24].O.C(#N)C>CN(C)C=O>[CH3:3][C:4]1([CH3:22])[N:8]([CH2:31][C:29]2[CH:28]=[CH:27][N:26]=[C:25]([CH2:23][CH3:24])[CH:30]=2)[C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[C:5]1=[O:21]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 132680675,5-Dimethyl-3-[4-(trifluoromethoxy)phenyl]imidazolidine-2,4-dioneHCID 18373917Acetonitrile--water (1/1)2×HCID 21874554HCID 21874554, compound

Product 1

HCID 596943455,5-Dimethyl-1-(2-ethylpyrid-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dioneYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.009 g of sodium hydride is added to a solution of 0.064 g of 5,5-dimethyl-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione in 1 ml of anhydrous dimethylformamide, under an inert atmosphere of argon, at a temperature in the region of 20° C. Stirring is continued at this temperature for 30 minutes. A solution of 0.062 g of 2-ethyl-4-(bromomethyl)pyridine in 0.5 ml of anhydrous dimethylformamide is added, followed by addition of ice-cold water after reaction for 10 minutes. The reaction mixture is placed on a cartridge 27 mm in diameter packed with 25 g of octadecyl-grafted 40-60 μm silica conditioned successively with the mixture (water/acetonitrile) (5/95) (v/v) and then with the mixture (water/acetonitrile) (95/5) (v/v). The elution is performed with a mixture (water/acetonitrile) (95/5) (v/v) over 20 minutes, followed by a linear gradient of from 5% to 95% acetonitrile over 60 minutes, at a flow rate of 10 ml/minute. The fractions between 750 and 790 ml are concentrated under reduced pressure. 0.06 g of 5,5-dimethyl-1-(2-ethylpyrid-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione is thus obtained, the characteristics of which product are as follows:

Workup

  1. additionfollowed by addition of ice-cold water
  2. customafter reaction for 10 minutes
  3. washThe elution
  4. waitis performed with a mixture (water/acetonitrile) (95/5) (v/v) over 20 minutes
  5. waitfollowed by a linear gradient of from 5% to 95% acetonitrile over 60 minutes, at a flow rate of 10 ml/minute
  6. concentrationThe fractions between 750 and 790 ml are concentrated under reduced pressure

Sources & evidence

ORD record
ord-f74da3ed14ba4dbaab13cb064dd595ed
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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