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

HRID 546553노트

반응식

HRID 546553 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-ee98f11469764720a1c68ef92190dcf6
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935819B2

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