(Diethylamino)sulfur trifluoride → 2-Chloro-5-fluoro-4-(1-fluoro-1-methyl-ethyl)pyrimidine

HRID 470194노트

반응식

HRID 470194 반응식
C(N(S(F)(F)[F:7])CC)C.[Cl:10][C:11]1[N:16]=[C:15]([C:17](O)([CH3:19])[CH3:18])[C:14]([F:21])=[CH:13][N:12]=1>ClCCl>[Cl:10][C:11]1[N:16]=[C:15]([C:17]([F:7])([CH3:19])[CH3:18])[C:14]([F:21])=[CH:13][N:12]=1

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 866978842-(2-Chloro-5-fluoropyrimidin-4-yl)propan-2-ol

생성물 1

HCID 866978852-Chloro-5-fluoro-4-(1-fluoro-1-methyl-ethyl)pyrimidine수율 87%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

Diethylaminosulfur trifluoride (6.53 g, 40.5 mmol) is added drop wise to a −78° C. solution of 2-(2-chloro-5-fluoro-pyrimidin-4-yl)propan-2-ol (4.825 g, 25.31 mmol) in dichloromethane (70 mL) under nitrogen. The reaction is stirred at −78° C. for 30 minutes under nitrogen, is then quenched with aqueous saturated sodium bicarbonate and is warmed to room temperature. The reaction mixture is extracted three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated under vacuum. The resulting crude product is purified over silica gel with a 40 minute, 5% to 100% ethyl acetate in hexanes gradient to give the title compound (4.23 g, 87%). ES/MS (m/e): (35Cl/37Cl) 193/195 (M+H).

후처리

  1. customis then quenched with aqueous saturated sodium bicarbonate
  2. temperatureis warmed to room temperature
  3. extractionThe reaction mixture is extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe resulting crude product is purified over silica gel with a 40 minute

출처 및 근거

ORD 기록
ord-1d7974083cca4c31aa29f626706d54eb
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629270B2

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