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

HRID 227765노트

반응식

HRID 227765 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ee8026995d140daa05c5efb2b38b35d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560551B2

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