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Method for synthesizing fluorine-containing pyrimidinone compound

A technology for fluorine-containing pyrimidone and a synthesis method, which is applied in the field of synthesis of fluorine-containing pyrimidone compounds, can solve the problems of high cost, unfriendly environment, limited synthesis method, etc., and achieves low cost, environment-friendly and simple reaction system. Effect

Inactive Publication Date: 2018-06-29
QINGDAO AGRI UNIV
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Problems solved by technology

[0003] However, the current synthetic methods for the synthesis of trifluoroalkyl-substituted pyrimidinones are very limited.
The equivalent amount of metal manganese acetate is used in a relatively mature synthesis method, and acetic acid is used as a solvent for the reaction. However, excessive metal reagents and excessive organic solvents in the reaction are not friendly to the environment, and the cost is high, so it is not suitable for industrial production.

Method used

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  • Method for synthesizing fluorine-containing pyrimidinone compound
  • Method for synthesizing fluorine-containing pyrimidinone compound
  • Method for synthesizing fluorine-containing pyrimidinone compound

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preparation example Construction

[0021] The embodiment of the present invention provides a method for synthesizing fluoropyrimidinone compounds, comprising the following steps:

[0022] Pyrimidinone compounds and sodium trifluoromethanesulfinate are respectively added into the reaction bottle, and reacted at 25° C.-80° C. for 2-4 hours under the action of tert-butyl perbenzoate and water.

[0023] In this step, pyrimidinone compounds and sodium trifluoromethylsulfinate are used to synthesize fluorine-containing pyrimidinone compounds. In this step, sodium trifluoromethylsulfinate generates trifluoromethyl cations under the action of TBPB, and trifluoromethyl cations electrophilically attack pyrimidinone compounds, and then leave hydrogen ions to generate target products. It should also be noted here that this step does not require the participation of an organic solvent, and only water needs to be used as a solvent, which is not only environmentally friendly, but also can effectively increase the product yiel...

Embodiment 1

[0040] Add 1mmol of pyrimidinone compound, 1mmol of sodium trifluoromethyl sulfinate, 2mmol of tert-butyl perbenzoate and 1mL of water into a reaction tube, and react at 25°C for 2 hours. After the reaction is completed, the column chromatographic separation yields the following target: Compound:

[0041] Carry out nuclear magnetic spectrum analysis to above-mentioned white crystal powder, data is as follows:

[0042] 1 H NMR (DMSO-d6, 400MHz): δ13.64(s, 1H), 8.18(d, J=7.5Hz, 2H), 7.69(t, J=7.3Hz, 1H), 7.49-7.61(m, 7H );

[0043] 13 C NMR (DMSO-d6, 100MHz): d 165.5, 160.9, 159.8, 138.8, 133.3, 131.8, 130.1, 129.1, 129.0, 128.60, 128.57, 128.3, 123.9, 110.9;

[0044] After identification, the spectral data corresponded to the structural formula, proving that the synthesized product was 2,6-diphenyl-5-(trifluoromethyl)pyrimidin-4(3H)-one with a yield of 96%.

Embodiment 2

[0046] Add 1mmol of pyrimidinone compound, 1mmol of sodium trifluoromethyl sulfinate, 2mmol of tert-butyl perbenzoate and 1mL of water into a reaction tube, react at 65°C for 4 hours, and separate by column chromatography after the reaction, the following target is obtained Compound:

[0047] Carry out nuclear magnetic spectrum analysis to above-mentioned white crystal powder, data is as follows:

[0048] 1 H NMR (DMSO-d6, 400MHz): δ13.59(s, 1H), 8.25(d, J=7.0Hz, 2H), 7.74(d, J=7.7Hz, 2H), 7.68-7.40(m, 5H );

[0049] 13 C NMR (DMSO-d6, 100MHz): d 164.3, 160.9, 158.0, 137.6, 133.4, 132.0, 131.8, 130.9, 129.1, 129.0, 123.8, 123.8;

[0050] After identification, the spectral data corresponded to the structural formula, proving that the synthesized product was 6-(4-bromophenyl)-2-phenyl-5-(trifluoromethyl)pyrimidin-4(3H)-one, and the yield was 97%.

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Abstract

The invention provides a method for synthesizing a fluorine-containing pyrimidinone compound, and belongs to the field of organic synthesis. The method does not use a metal reagent and an organic solvent, is environmentally friendly, and is suitable for industrial production. The method comprises the following steps: separately adding the pyrimidinone compound and sodium trifluoromethylsulfinate into a reaction flask for reacting under the action of tert-butyl peroxybenzoate (TBPB) and water at temperature of 25 DEG C to 80 DEG C for 2 to 4 hours; and after completion of the reaction, performing column chromatography to obtain the fluorine-containing pyrimidinone compound. The method can be applied to the synthesis of a trifluoroalkyl-substituted pyrimidinone compound.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing fluorine-containing pyrimidinone compounds. Background technique [0002] Pyrimidinone is a very important structural unit, which plays a very extensive and important role in biomedicine, and is one of the mother core structures with the most potential to become a drug. On the one hand, its chemical properties are stable and there are many sites available for modification. On the other hand, due to the special properties of fluorine atoms and fluorine-containing groups, fluorine-containing compounds have attracted extensive attention in the field of medicine. [0003] However, the current synthetic methods for the synthesis of trifluoroalkyl-substituted pyrimidinones are very limited. The equivalent amount of metal manganese acetate is used in a relatively mature synthesis method, and acetic acid is used as a solvent for the reaction. However, the exces...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/36
Inventor 董道青丁彩真王艳丽杨洪迪田宝玲王祖利
Owner QINGDAO AGRI UNIV
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