Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of 5-fluoro-2-methylsulfonyl-4-aminopyrimidine

A technology of methanesulfonyl pyrimidine and methanesulfonyl group, which is applied in the field of preparation of 5-fluoro-2-methanesulfonyl-4-aminopyrimidine, can solve unseen problems and the like, achieves convenient operation, and is beneficial to separation and purification , the effect of simple synthesis process

Inactive Publication Date: 2019-08-16
DALIAN UNIV
View PDF9 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the basis of extensive literature research, there is no suitable method for the preparation of 5-fluoro-2-methylsulfonyl-4-amino, so it is necessary to develop a synthetic route for the preparation of this compound

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
  • Preparation method of 5-fluoro-2-methylsulfonyl-4-aminopyrimidine
  • Preparation method of 5-fluoro-2-methylsulfonyl-4-aminopyrimidine
  • Preparation method of 5-fluoro-2-methylsulfonyl-4-aminopyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] This embodiment is a preparation method of 5-fluoro-2-methanesulfonyl-4-aminopyrimidine, according to the following reaction formula:

[0020]

[0021] The specific experimental process is as follows:

[0022] Using a three-necked flask, add 4.21g (0.02mol, 96%, 1eq) of newly prepared 4-chloro-5-fluoro-2-methanesulfonylpyrimidine, 20ml of tetrahydrofuran, and add ammonia water 3.09g (0.04mol , 25%, 2eq), after the completion of the dropwise reaction for 3 to 5 hours, the solvent THF was removed under reduced pressure after the reaction was completed, and 20 mL of water was added to the residue of the kettle. After cooling, a solid precipitated out, and a large amount of brown solid was obtained by filtration. After drying, it was recrystallized and columnar. Chromatography gave 2.48 g of brown solid product 5-fluoro-2-methylsulfonyl-4-aminopyrimidine, GC: 98%, yield 65%.

Embodiment 2

[0024] This embodiment is a preparation method of 5-fluoro-2-methanesulfonyl-4-aminopyrimidine, according to the following reaction formula:

[0025]

[0026] The specific experimental process is as follows:

[0027] Using a three-necked flask, add 4.21g (0.02mol, 96%, 1eq) of newly prepared 4-chloro-5-fluoro-2-methanesulfonylpyrimidine, 20ml of tetrahydrofuran, and add ammonia water 4.63g (0.06mol , 25%, 3eq), after the completion of the dropwise reaction for 3 to 5 hours, the solvent THF was removed under reduced pressure after the reaction was completed, and 20 mL of water was added to the residue of the kettle. After cooling, solids were precipitated, and a large amount of brown solids were obtained by filtration. After drying, they were recrystallized and columnar. Chromatography gave 2.79 g of brown solid product 5-fluoro-2-methanesulfonyl-4-aminopyrimidine, GC: 98%, yield 73%.

Embodiment 3

[0029] This example is the preparation method of 4-chloro-5-fluoro-2-methylsulfonyl pyrimidine, according to the following reaction formula:

[0030]

[0031] The specific experimental process is as follows:

[0032] Using a three-necked flask, add 4.21g (0.02mol, 96%, 1eq) of newly prepared 4-chloro-5-fluoro-2-methanesulfonylpyrimidine, 20ml of tetrahydrofuran, and add ammonia water 4.63g (0.06mol , 25%, 3eq), after the dropwise addition, react for 8-10h, remove the solvent tetrahydrofuran under reduced pressure after the reaction is completed, add 20mL water to the residue of the kettle, after cooling, solids are precipitated, and a large amount of brown solids are obtained by filtration, after drying, recrystallization and column Chromatography gave 3.06 g of brown solid product 5-fluoro-2-methanesulfonyl-4-aminopyrimidine, GC: 98%, yield 80%.

[0033] According to embodiment 1,2, increase the molar weight of ammoniacal liquor, the yield of product is promoted to 73% by...

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 preparation method of 5-fluoro-2-methylsulfonyl-4-aminopyrimidine, and belongs to the technical field of organic chemistry. The method comprises the following steps: performing an amination reaction by using 4-chloro-5-fluoro-2-methylsulfonylpyrimidine and ammonia water as raw materials and tetrahydrofuran as a solvent at room temperature to form a mixture of the 5-fluoro-2-methylsulfonyl-4-aminopyrimidine and other impurities, performing recrystallization, and performing column chromatography to obtain the 5-fluoro-2-methylsulfonyl-4-aminopyrimidine pure product, wherein the yield is 65-80%. The preparation method provided by the invention makes up for deficiency of a current synthetic process, and the novel method for synthesizing the 5-fluoro-2-methylsulfonyl-4-aminopyrimidine is provided.

Description

technical field [0001] The invention relates to a preparation method of 5-fluoro-2-methanesulfonyl-4-aminopyrimidine, which belongs to the field of fine chemical intermediates. Background technique [0002] 5-Fluoro-2-methylsulfonyl-4-aminopyrimidine is an important fluorine-containing pesticide and pharmaceutical intermediate, which can be used to synthesize compounds with antitumor activity and prepare herbicides, fungicides, appetite suppressants, etc. Applied in the field of medicine and health. The pyrimidine compound has good biological activity, can be effectively antibacterial and has antitumor activity. Therefore, the compound has high application value in biomedicine. [0003] In the currently existing methods for synthesizing 5-fluoro-2-methanesulfonyl-4-aminopyrimidine, the reaction conditions are harsh, and a large amount of waste liquid will be generated during the reaction. On the basis of extensive literature research, there is no suitable method for prepa...

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): C07D239/47
CPCC07D239/47
Inventor 王爱玲张腾崔颖娜王肖肖王帆郑学仿
Owner DALIAN UNIV