Method for preparing 4-amino-3-(4-aminobenzene)furo[2,3-d] pyrimidine

An aminobenzene, 3-d technology, applied in the field of chemistry, can solve the problems of environmental pollution, complex preparation process, low yield, etc., and achieve the effects of environmental friendliness, easy post-processing, and simple reaction

Inactive Publication Date: 2015-01-28
SHANGHAI INST OF TECH
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Aiming at the above-mentioned technical problems in the above-mentioned prior art, the present invention provides a method for preparing 4-amino-3-(4-aminobenzene)furo[2,3-d]pyrimidine, the preparation method Solve the technical problems of complex preparation process, low yield and serious environmental pollution in the prior art

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing 4-amino-3-(4-aminobenzene)furo[2,3-d] pyrimidine
  • Method for preparing 4-amino-3-(4-aminobenzene)furo[2,3-d] pyrimidine
  • Method for preparing 4-amino-3-(4-aminobenzene)furo[2,3-d] pyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0038] Synthesis of compound (2)

[0039]

[0040] In a 500mL single-necked bottle, add p-nitroacetophenone (63.74g, 386mmol), N-bromosuccinimide (68.77g, 386.4mmol), p-toluenesulfonic acid monohydrate (73.33g, 386mmol) With 200 mL of acetonitrile, react at 50°C for 24 hours. TLC showed that the reaction was complete, the solvent was evaporated under reduced pressure, the residue was neutralized to neutrality by adding saturated sodium bicarbonate solution, extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, evaporated under reduced pressure, washed with petroleum ether to obtain a yellow Solid (82.9 g, 88.0%).

[0041] Synthesis of compound (3)

[0042]

[0043] Add compound 2 (82.9g, 0.34mol), sodium acetate (70.7g, 0.68mol), tetrabutylammonium bromide (2.2g, 6.8mmol) and 425mL toluene into a 1000mL single-necked bottle, and react at 75°C for 1 hour , the solution turned from yellow to brown to produce a black solid, and TLC show...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a method for preparing 4-amino-3-(4-aminobenzene)furo[2,3-d] pyrimidine. The method comprises the following steps: using nitroacetophenone as a raw material, reacting the nitroacetophenone and N-bromo-succinimide to generate 2-bromo-1-(4-nitrophenyl)aceton by using para-toluenesulfonic acid as a catalyst, further reacting the 2-bromo-1-(4-nitrophenyl)aceton, sodium acetate and tetrabutylammonium bromide to generate 2-acetoxyl-1-(4-nitrophenyl)aceton, through reducing nitro into amino, reacting the 2-bromo-1-(4-nitrophenyl)aceton and hydrochloric acid, and reducing acetoxyl group into hydroxy to obtain 1-(4-aminophenyl)-2-hydroxy-aceton; then reacting the 1-(4-aminophenyl)-2-hydroxy-aceton, malononitrile and diethylamine to obtain 2-amino-4-(4-aminophenyl)-3-furan nitrile; finally reacting the 2-amino-4-(4-aminophenyl)-3-furan nitrile and formamidine acetate to obtain the 4-amino-3-(4-aminobenzene)furo[2,3-d] pyrimidine. The method has the advantages that the operation is simple and the total recovery is high.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a pharmaceutical intermediate 4-amino-3-(4-aminobenzene)furo[2,3-d]pyrimidine, specifically a method for preparing 4-amino-3-( 4-aminophenyl)furo[2,3-d]pyrimidine method. [0002] Background technique [0003] Animal experiments have shown that furo[2,3-d]pyrimidine derivatives, as receptor-interacting protein 1 (RIP1) enzyme inhibitors, have good curative effects on diseases related to cell necrosis, such as: brain, retina and kidney defects Blood / reperfusion injury, myocardial infarction, retinal detachment, inflammation, gastrointestinal and skin diseases, etc. Therefore, furo[2,3-d]pyrimidine derivatives play an important role in future pharmaceutical research and development. [0004] For the synthesis of furo[2,3-d]pyrimidine derivatives——4-amino-3-(4-aminobenzene)furo[2,3-d]pyrimidine, the following methods have been reported in the literature, but all There are th...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048
CPCC07C201/12C07C201/16C07C221/00C07D307/68C07D491/048C07C205/45C07C225/22
Inventor 鲁彦郭建宇王进高东刘境廷戴安妮高珏
Owner SHANGHAI INST OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap