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4-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol → 6-{[3-chloro-5-(2-methoxyethoxy)pyridin-2-yl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)quinazoline-4-amine

HRID 81663
笔记
打印预览

反应方程式

HRID 81663 反应方程式
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[CH3:20][N:21]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([OH:37])[CH:35]=3)[N:30]=[CH:29][N:28]=2)=[N:22]1.O.[Cl-].[Na+]>C(Cl)(Cl)Cl.CN(C)C(=O)C>[Cl:8][C:7]1[C:2]([O:37][C:34]2[CH:35]=[C:36]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][N:28]=[C:27]3[NH:26][C:23]2[CH:24]=[CH:25][N:21]([CH3:20])[N:22]=2)=[N:3][CH:4]=[C:5]([O:9][CH2:10][CH2:11][O:12][CH3:13])[CH:6]=1
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

7

反应物 4

HCID 231603824-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-olHCID 23665647叔丁醇钾HCID 57417360Sodium chloride; waterHCID 866459022,3-Dichloro-5-(2-methoxyethoxy)pyridine

产物 1

HCID 595088886-{[3-chloro-5-(2-methoxyethoxy)pyridin-2-yl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)quinazoline-4-amine收率 28.1%

试剂、催化剂与溶剂 2

HCID 6212三氯甲烷溶剂
HCID 31374N,N-二甲基乙酰胺溶剂

反应条件

温度
180 °C

实验过程

2,3-Dichloro-5-(2-methoxyethoxy)pyridine (127 mg, 0.57 mmol) and potassium tert-butoxide (70 mg, 0.62 mmol) were added to an N,N-dimethylacetamide solution (2 ml) of 4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol (60 mg, 0.25 mmol), and stirred overnight at 180° C. under a nitrogen atmosphere in a sealed tube. The reaction solution was cooled with ice, then sodium chloride water and chloroform were added, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by reversed-phase liquid chromatography (YMC CombiPrep Pro C18 AS-360-CC) to obtain the entitled compound (30 mg, yield: 28%) as a pale orange amorphous solid.

后处理

  1. temperatureThe reaction solution was cooled with ice
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by reversed-phase liquid chromatography (YMC CombiPrep Pro C18 AS-360-CC)

来源与证据

ORD记录
ord-8cfc7015865c40fcbf15d36aa65d671e
来源数据集
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08846700B2

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记