Sodium hydride → N-(1-methyl-1H-pyrazol-3-yl)-6-[(6-nitropyridin-3-yl)oxy]quinazoline-4-amine

HRID 81623

반응식

HRID 81623 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[H-].[Na+].[CH3:13][N:14]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=3)[N:23]=[CH:22][N:21]=2)=[N:15]1>CN(C)C=O>[CH3:13][N:14]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][C:2]4[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=4)[CH:28]=3)[N:23]=[CH:22][N:21]=2)=[N:15]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 8176205-Bromo-2-nitropyridineHCID 231603824-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol

생성물 1

HCID 68431306N-(1-methyl-1H-pyrazol-3-yl)-6-[(6-nitropyridin-3-yl)oxy]quinazoline-4-amine수율 77%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

5-Bromo-2-nitropyridine (460 mg, 2.3 mmol) and sodium hydride (120 mg, 3.1 mmol) were added to an N,N-dimethylformamide suspension (10 ml) of 4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol (500 mg, 2.1 mmol), and stirred at 60° C. for 14 hours. The reaction solution was cooled to room temperature, the precipitate was collected by filtration, washed with water. The obtained precipitate was dried, then purified by silica gel column chromatography (chloroform:methanol=96:4) to obtain N-(1-methyl-1H-pyrazol-3-yl)-6-[(6-nitropyridin-3-yl)oxy]quinazoline-4-amine (580 mg, yield: 77%) as a pale yellow solid.

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customThe obtained precipitate was dried
  5. custompurified by silica gel column chromatography (chloroform:methanol=96:4)

출처 및 근거

ORD 기록
ord-937af315ca2148cd8e5b0d69ad08bec1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846700B2

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