4-Aminophenol → 4-{3-[2-(Methylthio)pyrimidin-4-yl]pyridin-2-yloxy}benzeneamine

HRID 252646

반응식

HRID 252646 반응식
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[CH3:15][S:14][C:10]1[N:9]=[C:8]([C:7]2[C:2]([O:23][C:20]3[CH:21]=[CH:22][C:17]([NH2:16])=[CH:18][CH:19]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:12][N:11]=1

참가 물질

6

반응물 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 577562394-(2-Chloropyridin-3-yl)-2-(methylthio)pyrimidine

생성물 1

HCID 667319134-{3-[2-(Methylthio)pyrimidin-4-yl]pyridin-2-yloxy}benzeneamine

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
130 °C

실험 절차

A resealable pressure bottle was charged with 4-(2-chloropyridin-3-yl)-2-(methylthio)pyrimidine (2.85 g, 12.00 mmol), 4-aminophenol (1.44 g, 26.5 mmol), and cesium carbonate (1.44 g, 13.20 mmol). These reagents were suspended in DMSO (24 ml, 0.50 M), and the vessel was sealed and mixture heated to 130° C. for 48 h. The reaction mixture was allowed to cool to RT, diluted with water and extracted with ethyl acetate. The organic layer was collected, dried with Na2SO4, filtered, and concentrated to give light brown residue, which was purified by silica gel chromatography (ISCO, 10% to 50% Ethyl Acetate/Hexanes) to afford 4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy)benzenamine as a light yellow solid. MS m/z=311 [M+H]+. Calc'd for C16H14N4OS: 310.37.

후처리

  1. customthe vessel was sealed
  2. temperatureto cool to RT
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was collected
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give light brown residue, which
  9. customwas purified by silica gel chromatography (ISCO, 10% to 50% Ethyl Acetate/Hexanes)

출처 및 근거

ORD 기록
ord-42cedb53d6a24c43acdd5e2760472cfa
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868177B2

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