Tetrahydropyridinopyrimidine compound and preparation method and application thereof

A technology for tetrahydropyridine and pyrimidine, which is applied in the field of compounds and their preparation, can solve problems such as limited synthesis methods, and achieve the effects of high atom economy, green raw materials, and cheap and easily available raw materials

Active Publication Date: 2020-03-10
WUYI UNIV
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this strategy requires the pre-preparation of pyridopyrimidines, and the related synthetic methods are very limited

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
  • Tetrahydropyridinopyrimidine compound and preparation method and application thereof
  • Tetrahydropyridinopyrimidine compound and preparation method and application thereof
  • Tetrahydropyridinopyrimidine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The tetrahydropyridopyrimidine compound described in this example is 2-phenyl-tetrahydropyridopyrimidine (compound shown in formula 3a), and the preparation method includes the following steps: in the reactor, add 1.0 mmol o-aminopyridinemethanol and 0.5 mmol of benzamidine, add 1% triruthenium dodecacarbonyl of the amount of ortho-aminopyridinemethanol substance, then add cesium carbonate of 50% of the amount of ortho-aminopyridinemethanol substance, add 1.5ml of methanol and 1.5ml of t- Pentanol, under nitrogen atmosphere, stirred and reacted at 70°C for 24 hours, cooled to room temperature after the reaction, diluted the reaction solution, filtered, and evaporated under reduced pressure to remove the solvent to obtain the crude product, which was purified by column chromatography The compound represented by formula 3a (yield 81%), the product was in the form of yellow oil.

[0042]

[0043] Compound hydrogen spectrogram and carbon spectrogram shown in formula 3a a...

Embodiment 2

[0051] The tetrahydropyridopyrimidine compound described in this example is 2-(4-methyl-phenyl)-tetrahydropyridopyrimidine (compound shown in formula 3b), and the preparation method comprises the following steps: in the reactor , add 0.5 mmol o-aminopyridinemethanol and 1.0 mmol p-toluidine, add 3% cyclopentadienyl bis(triphenylphosphine) ruthenium(II) chloride to the amount of o-aminopyridinemethanol , then add 100% potassium tert-butoxide in the amount of o-aminopyridinemethanol, add 1.5ml isopropanol and 1.5ml tert-amyl alcohol, stir and react at 150°C for 8 hours, cool to room temperature after the reaction, and dilute the reaction solution , filtered, and the solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, which was purified by column chromatography to obtain the compound shown in formula 3b (80% yield), which was in the form of yellow oil.

[0052]

[0053] The hydrogen spectrogram and the carbon spectrogram of the compoun...

Embodiment 3

[0061] The tetrahydropyridopyrimidine compound described in this example is 2-(4-chloro-phenyl)-tetrahydropyridopyrimidine (compound shown in formula 3c), and the preparation method includes the following steps: in the reactor, add 1.0 Millimoles of ortho-aminopyridinemethanol and 1.0 mmoles of 4-chloro-benzamidine, 3% dichloro(pentamethylcyclopentadienyl)iridium(III) dimer was added to the amount of ortho-aminopyridinemethanol substance (Catalyst, Cat.), add the potassium hydroxide of 50% of the amount of o-aminopyridinemethanol again, add 1.5ml ethanol and 1.5ml tert-amyl alcohol, under nitrogen atmosphere, stir reaction at 120 ℃ for 12 hours, react After cooling to room temperature, the reaction solution was diluted, filtered, and the solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, which was purified by column chromatography to obtain the compound represented by formula 3c (yield 78%).

[0062]

[0063] The hydrogen spectrogr...

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 tetrahydropyridinopyrimidine compound which has excellent inhibition effect on K562, HL-60, HeLa and BGC-823 cancer cells of testees. The compound can be used for in-vitro antitumor activity screening as an antitumor reagent and for antitumor medicines. The invention also discloses a preparation method of the tetrahydropyridinopyrimidine compound. The method achieves synthesis of the tetrahydropyridinopyrimidine compound, at medium to favorable yield, of an o-aminopyridine methanol substrate and different amidine salts, wherein the product can be widely applied to thefield of biomedicines and functional materials. The reaction is free of extra oxidants and inert gas protection. The method employs green, cheap and feasible raw materials, is simple in operation andhas great atomic economy. The invention also discloses the applications of the tetrahydropyridinopyrimidine compound for preparing antitumor reagents or tumor prevention and treatment drugs.

Description

technical field [0001] The invention relates to a compound and its preparation method and application, in particular to a tetrahydropyridopyrimidine compound and its preparation method and application. Background technique [0002] Tetrahydropyridopyrimidine is the core structural unit of a large number of alkaloids and functional molecules, exhibiting very good biological and pharmaceutical activities, such as the compounds shown in the following formulas (1)-(3). [0003] [0004] Generally speaking, the current synthesis method is to hydrogenate quinazoline under high-pressure hydrogen to obtain our target hydrogenated product, as shown in the following formula: [0005] [0006] The synthesis of such compounds can be achieved by high-pressure hydrogenation of pyridopyrimidines. However, this strategy requires the pre-preparation of pyridopyrimidines, and the related synthetic methods are very limited. Therefore, how to directly and effectively synthesize such sem...

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): C07D471/04A61K31/519A61P35/00
CPCA61P35/00C07D471/04
Inventor 陈修文何芊林梁婉仪钟明利陈世杰李亦彪朱忠智
Owner WUYI UNIV
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