4-substituent-2-amido pyrimidine compound and preparation method thereof

A technology for aminopyrimidines and compounds, which is applied in the field of preparation of 2-aminopyrimidines, can solve the problems that 4-substituted 2-aminopyrimidines are not universal, and achieve high yield, mild conditions and simple reaction process Effect

Inactive Publication Date: 2009-12-16
丹东恒悦新材料有限公司
View PDF0 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above two types of methods are not universal in the preparation of 4-substituted 2-aminopyrimidine compounds

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
  • 4-substituent-2-amido pyrimidine compound and preparation method thereof
  • 4-substituent-2-amido pyrimidine compound and preparation method thereof
  • 4-substituent-2-amido pyrimidine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the synthesis of 4-(2-pyridyl)-2-aminopyrimidine

[0019] Add 2-acetylpyridine (242g, 0.2mol) and 500ml N,N-dimethylformamide dimethyl acetal into a three-necked flask, stir well, then heat the mixture to reflux, reflux reaction for 4h, TLC tracking the end of the reaction After the reaction, the stirring was stopped, the reaction solution was cooled to room temperature, filtered, and dried. The crude product was recrystallized with chloroform / petroleum ether (volume ratio 1:1), and dried to obtain yellow solid compound (E)-3-(dimethylamino)-1-(pyridin-2-yl)-2-propene -1-one 264g, yield 75%.

[0020] Add sodium ethoxide (27.2g, 0.4mol) and 1000ml of absolute ethanol to a 2L three-necked flask, stir evenly, then add guanidine hydrochloride (38.3g, 0.4mol) to the bottle at one time, stir at room temperature for 1 hour, and obtain liquid A; The compound (E)-3-(dimethylamino)-1-(pyridin-2-yl)-2-propen-1-one (70.4g, 0.4mol) obtained in the previous step was d...

Embodiment 2

[0026] Embodiment 2: the synthesis of 4-(3-pyridyl)-2-aminopyrimidine

[0027] Add 3-acetylpyridine (242g, 0.2mol) and 500ml N,N-dimethylformamide dimethyl acetal into a three-necked flask, stir well, then heat the mixture to reflux, reflux reaction for 4h, TLC tracking the end of the reaction After the reaction, the stirring was stopped, the reaction solution was cooled to room temperature, filtered, and dried. The crude product was recrystallized with chloroform / petroleum ether (volume ratio 1:1), and dried to obtain orange crystal compound (E)-3-(dimethylamino)-1-(pyridin-3-yl)-2-propene -1-one 285g, yield 81%.

[0028] Add sodium ethoxide (27.2g, 0.4mol) and 1000ml of absolute ethanol to a 2L three-necked flask, stir evenly, then add guanidine hydrochloride (38.3g, 0.4mol) to the bottle at one time, stir at room temperature for 1 hour, and obtain liquid A; The compound (E)-3-(dimethylamino)-1-(pyridin-3-yl)-2-propen-1-one (70.4g, 0.4mol) obtained in the previous step was...

Embodiment 3

[0034] Example 3: Synthesis of 4-(4-pyridyl)-2-aminopyrimidine

[0035] Add 4-acetylpyridine (242g, 0.2mol) and 500ml N,N-dimethylformamide dimethyl acetal into a three-necked flask, stir well, then heat the mixture to reflux, reflux reaction for 4h, TLC tracking the end of the reaction After the reaction, the stirring was stopped, the reaction solution was cooled to room temperature, filtered, and dried. The crude product was recrystallized with chloroform / petroleum ether (volume ratio 1:1), and dried to obtain orange-yellow solid compound (E)-3-(dimethylamino)-1-(pyridin-4-yl)-2- 252 g of propen-1-one, yield 71.6%.

[0036] Add sodium methoxide (27.2g, 0.4mol) and 1000ml of absolute ethanol to a 2L three-necked flask, stir well, then add guanidine hydrochloride (38.3g, 0.4mol) to the bottle at one time, and stir at room temperature for 1 hour to obtain liquid A; The compound (E)-3-(dimethylamino)-1-(pyridin-4-yl)-2-propen-1-one (70.4g, 0.4mol) obtained in the previous step...

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 relates to a 4-substituent-2-amido pyrimidine compound and a preparation method thereof. The invention adopts a technical scheme of having a structure shown as general formula (I). The preparation method comprises the following steps that: an aromatic ring or heterocyclic ring compound with acetyl radicals is put into a container together with N, N-dimethyl formamide dimethyl acetal, and the mixture is evenly stirred, is heated until refluxing and reacts for 3 to 5 hours, the stirring is stopped, and the mixture is cooled to room temperature, filtered and dried to obtain an intermediate product; sodium ethylate or sodium methoxide is dissolved in absolute alcohol, the mixture is evenly stirred, guanidine hydrochloride is added into the mixture, the obtained mixture is stirred for 0.5 to 1.5 hours at room temperature, and A liquid is obtained; the intermediate product is dissolved in the absolute alcohol to obtain B liquid; and the B liquid is slowly dropped into the A liquid, the reaction system is heated until refluxing, the reaction is carried out for 5 to 7 hours, the stirring is stopped, and the obtained mixture is cooled to room temperature, stands overnight, is filtered, washed and dried. The invention has high yield, high purity, simple technology and universality.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to the preparation of a 2-aminopyrimidine compound with different substituents at the 4-position. Background technique [0002] 4-Substituted-2-aminopyrimidines are an important class of drugs and intermediates in organic synthesis, and are also widely used in other chemical fields. It is mainly used in the synthesis of antibacterial, anti-tumor, anti-allergic and certain other disease inhibitors in medicine; it can also be used in the synthesis of organic heterocyclic compounds and organic coordination compounds; it can also be used in metal corrosion inhibitors, mechanical Synthesis of antifouling and antioxidants. At present, there are two main synthetic routes of 2-aminopyrimidine compounds according to raw material classification: one is based on guanidine hydrochloride, nitrate, carbonate, etc. 3 The compound of structure is prepared by ring closure reac...

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): C07D401/04C07D409/04C07D405/04C07D239/42
Inventor 严欣宁张慧东石庆学李丹王冠中沈德全赵瑞佳
Owner 丹东恒悦新材料有限公司
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