二甲胺 → N-{4-[(3-bromophenyl)amino]quinazoline-6-yl}4-(dimethylamino)-2-butenamide

HRID 1069012笔记

反应方程式

HRID 1069012 反应方程式
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:23](=[O:28])[CH:24]=[CH:25][CH2:26]Br)[CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1.CN(C)C=O>[Br:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:23](=[O:28])[CH:24]=[CH:25][CH2:26][N:2]([CH3:3])[CH3:1])[CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1

参与物

7

反应物 4

HCID 674二甲胺HCID 8857乙酸乙酯HCID 516892碳酸氢钠HCID 544131234-[(3-Bromophenyl)amino]-6-[(4-bromo-1-oxo-2-buten-1-yl)amino]-quinazoline

产物 1

HCID 49826478N-{4-[(3-bromophenyl)amino]quinazoline-6-yl}4-(dimethylamino)-2-butenamide收率 44%

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺溶剂HCID 8028四氢呋喃溶剂2 次

实验过程

Twenty five milliliters of 2N dimethylamine in tetrahydrofuran were stirred and cooled in an ice bath, and a solution of 1.16 g (2.5 mmoles) of 4-Bromo-but-2-enoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide in 20 mL of tetrahydrofuran and 10 mL of N,N-dimethylformamide was added dropwise. After stirring for 2 hours, 45 mL of ethyl acetate and 30 mL of saturated aqueous sodium bicarbonate were added, and the layers were separated. The organic layer was extracted with 25 mL of brine, dried over sodium sulfate, and taken to an oil in vacuo. This was chromatographed on silica gel with 1:4 methanol methylene chloride to give 475 mg (44%) of the desired product, which melted at 215-217° C. Mass spectrum (m/e) M+2H 213.4, 214.4. M+H 426.1.

后处理

  1. temperaturecooled in an ice bath
  2. customthe layers were separated
  3. extractionThe organic layer was extracted with 25 mL of brine
  4. dry with materialdried over sodium sulfate
  5. customThis was chromatographed on silica gel with 1:4 methanol methylene chloride

来源与证据

ORD记录
ord-a203f332c18c4118913b0ae45579b961
来源数据集
uspto-grants-2001_06
专利号
US06251912B1

反应笔记

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