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

HRID 252646

反応式

HRID 252646 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-42cedb53d6a24c43acdd5e2760472cfa
出典データセット
uspto-grants-2011_01
特許番号
US07868177B2

関連ノート

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