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

HRID 1044604

반응식

HRID 1044604 반응식
[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

참가 물질

6

반응물 3

HCID 7047QuinolineHCID 24813Phosphorus oxychlorideHCID 178516143HCID 178516143, 화합물

생성물 1

HCID 115428814-Chloro-6-(trifluoromethyl)pyrimidine수율 21.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a5a3dcfe53094f62a33d367db9f32f0c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563582B2

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