Diethyl Ether → 2-(2-Chloro-5-fluoropyrimidin-4-yl)propan-2-ol

HRID 470193노트

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HRID 470193 반응식
[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[C:5]([F:11])=[CH:4][N:3]=1.[CH3:12][Mg]Br.C(OCC)C>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])([CH3:12])[CH3:9])[C:5]([F:11])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 865947381-(2-Chloro-5-fluoropyrimidin-4-yl)ethanoneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 866978842-(2-Chloro-5-fluoropyrimidin-4-yl)propan-2-ol수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A stirred, −78° C. solution of 1-(2-chloro-5-fluoro-pyrimidin-4-yl)ethanone (10.06 g, 57.6 mmol) in tetrahydrofuran (100 mL) under nitrogen is reacted with a 3 M solution of methyl magnesium bromide in diethyl ether (124 mL, 72.04 mmol) and the resulting mixture is stirred at −78° C. for 20 minutes. The reaction is quenched with aqueous saturated ammonium chloride and the mixture 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 crude product is purified over silica gel with a 30 minute, 5% to 100% ethyl acetate in hexanes gradient, to give the title compound (7.06 g, 64%). ES/MS (m/e): (35C/37Cl) 191/193 (M+H).

후처리

  1. customThe reaction is quenched with aqueous saturated ammonium chloride
  2. temperaturethe mixture is 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 crude product is purified over silica gel with a 30 minute

출처 및 근거

ORD 기록
ord-2a7797be6dd449df955cad82088e7e45
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629270B2

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