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

HRID 911150

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HRID 911150 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

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온도
130 °C

실험 절차

A resealable pressure bottle was charged with 4-(2-chloropyridin-3-yl)-2-(methylthio)pyrimidine (6.00 g, 25.2 mmol), 4-aminophenol (2.89 g, 26.5 mmol), and cesium carbonate (16.4 g, 50.5 mmol). These reagents were suspended in DMSO (50.5 ml, 0.50 M). The vessel was sealed and heated to 130° C. for 48 hrs. Reaction mixture was allowed to cool to RT, diluted with water and extracted with EtOAc. The organic layer was collected, dried with Na2SO4, filtered, and concentrated to give a light brown residue, which was purified by silica gel chromatography (ISCO, 10% to 50% Ethyl Acetate/Hexanes) to afford clean material as light yellow solid. MS m/z=311 [M+H]+. Calc'd for C16H14N4OS: 310.37.

후처리

  1. customThe vessel was sealed
  2. customReaction mixture
  3. temperatureto cool to RT
  4. extractionextracted with EtOAc
  5. customThe organic layer was collected
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a light brown residue, which
  10. customwas purified by silica gel chromatography (ISCO, 10% to 50% Ethyl Acetate/Hexanes)
  11. customto afford clean material as light yellow solid

출처 및 근거

ORD 기록
ord-9b462b1b6c944bc8881b404f1916135c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022221B2

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