Sodium hydride → 3-(4-Tert-butylphenyl)-5,5-dimethyl-1-{[2-(methylthio)pyrimidin-4-yl]methyl}imidazolidine-2,4-dione

HRID 546553Notes

Reaction equation

HRID 546553 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:14]2=[O:21])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl[CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([S:30][CH3:31])[N:25]=1>O1CCCC1>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15]([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([S:30][CH3:31])[N:25]=3)[C:14]2=[O:21])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 552634394-(Chloromethyl)-2-(methylthio)pyrimidineHCID 576259723-(4-Tert-butylphenyl)-5,5-dimethyl-imidazolidine-2,4-dione

Product 1

HCID 576259973-(4-Tert-butylphenyl)-5,5-dimethyl-1-{[2-(methylthio)pyrimidin-4-yl]methyl}imidazolidine-2,4-dioneYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 1.74 g of sodium hydride (60%) in 70 mL of tetrahydrofuran are successively added, dropwise under an inert atmosphere of argon, a solution of 4.52 g of 3-(4-tert-butylphenyl)-5,5-dimethyl-imidazolidine-2,4-dione obtained in stage c) in 25 mL of tetrahydrofuran, followed by a solution of 5.14 g of 4-(chloromethyl)-2-(methylthio)pyrimidine in 50 mL of tetrahydrofuran. After addition, the reaction mixture is refluxed for 48 hours, cooled to room temperature and poured into distilled water, and the aqueous phase is washed with ethyl acetate. The organic phase is then washed successively with water and saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with dichloromethane, to give 5.92 g of 3-(4-tert-butylphenyl)-5,5-dimethyl-1-{[2-(methylthio)pyrimidin-4-yl]methyl}imidazolidine-2,4-dione, the characteristics of which are as follows:

Workup

  1. additionare successively added, dropwise under an inert atmosphere of argon
  2. additionAfter addition
  3. temperaturethe reaction mixture is refluxed for 48 hours
  4. additionpoured
  5. distillationinto distilled water
  6. washthe aqueous phase is washed with ethyl acetate
  7. washThe organic phase is then washed successively with water and saturated sodium chloride solution
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is purified by chromatography on a column of silica
  12. washeluting with dichloromethane

Sources & evidence

ORD record
ord-ee98f11469764720a1c68ef92190dcf6
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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