4-Aminophenol → 4-(2-(4-Aminophenoxy)pyridin-3-yl)pyrimidin-2-amine

HRID 227765ノート

反応式

HRID 227765 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O.Cl[C:20]1[C:25]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH2:32])[N:27]=2)=[CH:24][CH:23]=[CH:22][N:21]=1>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:20]2[C:25]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH2:32])[N:27]=3)=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 4034-AminophenolHCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 533963354-(2-Chloropyridin-3-yl)pyrimidin-2-amine

生成物 1

HCID 577562184-(2-(4-Aminophenoxy)pyridin-3-yl)pyrimidin-2-amine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a resealable tube was added 4-aminophenol (1.3 g, 12 mmol), cesium carbonate (7.8 g, 24 mmol), and DMSO (16 ml, 0.75 M). The mixture was heated to 100° C. for 5 minutes, and then 4-(2-chloropyridin-3-yl)pyrimidin-2-amine (2.5 g, 12 mmol) was added, and the reaction mixture was heated to 130° C. overnight. Upon completion, as judged by LCMS, the reaction mixture was allowed to cool to RT and diluted with water. The resulting precipitate was filtered, and the solid washed with water and diethyl ether. The solid was then taken up in 9:1 CH2Cl2:MeOH and passed through a pad of silica gel with 9:1 CH2Cl2:MeOH as eluent. The solvent was concentrated in vacuo to provide the desired product, 4-(2-(4-aminophenoxy)pyridin-3-yl)pyrimidin-2-amine. MS m/z=280 [M+1]+. Calc'd for C15H13N5O: 279.30.

後処理

  1. temperaturethe reaction mixture was heated to 130° C. overnight
  2. temperatureto cool to RT
  3. filtrationThe resulting precipitate was filtered
  4. washthe solid washed with water and diethyl ether
  5. concentrationThe solvent was concentrated in vacuo

出典と根拠

ORDレコード
ord-9ee8026995d140daa05c5efb2b38b35d
出典データセット
uspto-grants-2009_07
特許番号
US07560551B2

反応ノート

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