Ethyl Acetate → (2-Chloropyrimidin-4-yl)quinolin-3-ylamine

HRID 495448노트

반응식

HRID 495448 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.CCN(C(C)C)C(C)C.CCOC(C)=O>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 113753-AminoquinolineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

생성물 1

HCID 22326846(2-Chloropyrimidin-4-yl)quinolin-3-ylamine

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 2,4-dichloropyrimidine (1.0 g, 6.7 mmol), 3-aminoquinoline (1.1 g, 7.79 mmol) and DIEA (2.0 mL, 11.5 mmol) in IPA (8 mL) was heated to reflux for 48 h. The mixture was poured into EtOAc (200 mL) and washed with H2O (100 mL). The organics were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified via medium pressure liquid chromatography using 50:50 EtOAc/hexanes followed by 100% EtOAc followed by 5:95 MeOH/CH2Cl2 followed by 1.0:10:90 conc. NH4OH/MeOH/CH2Cl2 as the solvent system. (2-Chloropyrimidin-4-yl)-quinolin-3-yl-amine was obtained as a tan solid.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. washwashed with H2O (100 mL)
  4. dry with materialThe organics were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified via medium pressure liquid chromatography

출처 및 근거

ORD 기록
ord-dcd88f54e0b249edb201d535306f0c55
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939874B2

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