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

HRID 338066ノート

反応式

HRID 338066 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-16546ef09df94f6382773454c75146a6
出典データセット
uspto-grants-2014_11
特許番号
US08889856B2

反応ノート

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