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

HRID 593965

反応式

HRID 593965 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 (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.

後処理

  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

出典と根拠

ORDレコード
ord-27b7ca24830748aa93424480e54c23af
出典データセット
uspto-grants-2016_01
特許番号
US09242961B2

関連ノート

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