Quinoline → 4-Chloro-6-(trifluoromethyl)pyrimidine

HRID 1044604

反応式

HRID 1044604 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[CH:7][N:6]=[C:5](O)[CH:4]=1.P(Cl)(Cl)([Cl:14])=O.N1C2C(=CC=CC=2)C=CC=1>C1(C)C=CC=CC=1.O>[Cl:14][C:5]1[CH:4]=[C:3]([C:2]([F:11])([F:10])[F:1])[N:8]=[CH:7][N:6]=1

参加物

6

反応物 3

HCID 7047QuinolineHCID 24813Phosphorus oxychlorideHCID 178516143HCID 178516143、化合物

生成物 1

HCID 115428814-Chloro-6-(trifluoromethyl)pyrimidine収率 21.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of 6-(trifluoromethyl)pyrimidin-4-ol (5.0 g, 30.5 mmol), phosphoryl chloride (3.41 mL, 36.6 mmol), and quinoline (2.16 mL, 18.3 mmol) in toluene (50 mL) was stirred at 100° C. for 5 h. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (10% EtOAc/Hexane) to yield the desired product (1.20 g, 21.6%). 1H NMR (400 MHz, CDCl3): 9.21 ppm (1H, s), 7.78 (1H, s).

後処理

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography (10% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-a5a3dcfe53094f62a33d367db9f32f0c
出典データセット
uspto-grants-2013_10
特許番号
US08563582B2

関連ノート

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