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Sodium Hydroxide → (2S)-7-chloro-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 633711
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HRID 633711 반응식
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[N:8]=[C:9]2[NH:16][C@:15]([CH3:21])([C:17]([F:20])([F:19])[F:18])[CH2:14][N:10]2[C:11](=[O:13])[CH:12]=1.[OH-].[Na+]>ClCCCl.O.C(OCC)(=O)C>[Cl:3][C:7]1[N:8]=[C:9]2[NH:16][C@:15]([CH3:21])([C:17]([F:20])([F:19])[F:18])[CH2:14][N:10]2[C:11](=[O:13])[CH:12]=1
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참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 136069601(2S)-7-hydroxy-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

생성물 1

HCID 136069597(2S)-7-chloro-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one수율 53%

시약·촉매·용매 3

HCID 111,2-Dichloroethane
용매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

41.60 mL (446.50 mmol) of phosphorus oxychloride are added, at room temperature and under an argon atmosphere, to a suspension of 35 g (148.80 mmol) of (S)-7-hydroxy-2-methyl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one in 350 mL of 1,2-dichloroethane. The resulting mixture is then heated at 70° C. for 4 hours. After cooling, the reaction mixture is evaporated to dryness under vacuum. The residue obtained is taken up in 35 mL of cold water and 500 mL of ethyl acetate. 32% sodium hydroxide is added to the mixture obtained, to pH=6-7. The organic phase is then separated out and then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 20 g of (S)-7-chloro-2-methyl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one, the characteristics of which are as follows:

후처리

  1. temperatureAfter cooling
  2. customthe reaction mixture is evaporated to dryness under vacuum
  3. customThe residue obtained
  4. customobtained, to pH=6-7
  5. customThe organic phase is then separated out
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-709d5c575cdd4029a65765bd9d5f7af6
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321790B2

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