Dihydrogen phosphate ionic liquid promotes the method for synthesizing dihydropyrimidinone compounds

A technology of dihydropyrimidinones and dihydrogen phosphate, applied in the field of synthesis of dihydropyrimidinones, to achieve the effects of simple preparation process, high catalytic activity, simple operation and post-treatment process

Active Publication Date: 2021-10-26
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there have been no articles or related patents reporting its application in promoting the synthesis of dihydropyrimidinone compounds

Method used

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  • Dihydrogen phosphate ionic liquid promotes the method for synthesizing dihydropyrimidinone compounds
  • Dihydrogen phosphate ionic liquid promotes the method for synthesizing dihydropyrimidinone compounds
  • Dihydrogen phosphate ionic liquid promotes the method for synthesizing dihydropyrimidinone compounds

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Experimental program
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Effect test

Embodiment 1

[0018] Add 0.05mmol [DMEA][H 2 PO 4 ] and 0.01mol CuI, 0.1mmol N-propargyl benzamide and 0.12mmol p-toluenesulfonyl azide, stirred and mixed on a magnetic stirrer, and then placed the reaction flask in an oil bath at 70 ° C to heat and stir the reaction 30min, the whole reaction process is tracked and monitored with TLC, after the reaction finishes, extract the reaction mixture with secondary water and dichloromethane, combine the dichloromethane phases, distill under reduced pressure and spin-dry the solvent, and the crude product is recrystallized (normal hexane: ethyl acetate Ester=7:1, v / v) to obtain the target product with a yield of 78%.

Embodiment 2

[0020] Add 0.05mmol [DMEA][H 2 PO 4 ] and 0.01mol CuI, 0.1mmol N-propargyl-4-methylbenzamide and 0.12mmol p-toluenesulfonyl azide, stirred and mixed on a magnetic stirrer, and then placed the reaction flask in an oil bath at Heated and stirred at 70°C for 30 min. The entire reaction process was tracked and monitored by TLC. After the reaction, the reaction mixture was extracted with secondary water and dichloromethane, the dichloromethane phase was combined, the solvent was distilled and spin-dried under reduced pressure, and the crude product was recrystallized ( n-hexane:ethyl acetate=7:1, v / v) to obtain the target product with a yield of 82%.

Embodiment 3

[0022] Add 0.05mmol [DMEA][H 2 PO 4 ] and 0.01mol CuI, 0.1mmol N-propargyl-3-methylbenzamide and 0.12mmol p-toluenesulfonyl azide, stirred and mixed on a magnetic stirrer, and then placed the reaction flask in an oil bath at Heated and stirred at 70°C for 30 min. The entire reaction process was tracked and monitored by TLC. After the reaction, the reaction mixture was extracted with secondary water and dichloromethane, the dichloromethane phase was combined, the solvent was distilled and spin-dried under reduced pressure, and the crude product was recrystallized ( n-Hexane:ethyl acetate=7:1, v / v) to obtain the target product with a yield of 80%.

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Abstract

The invention discloses a method for promoting the synthesis of dihydropyrimidinone compounds by dihydrogen phosphate ionic liquid, and belongs to the technical field of synthesis of dihydropyrimidinone compounds. The main points of the technical scheme of the present invention are: taking N-propargyl amide compound and p-toluenesulfonyl azide as the reaction substrate, CuI as the catalyst, and dihydrogen phosphate ionic liquid as the cocatalyst and solvent, stirring and reacting at 70°C The target product dihydropyrimidinone compounds were obtained. The preparation process of the dihydrogen phosphate ionic liquid in the present invention is simple, cheap and easy to obtain, and has high catalytic activity, which effectively promotes the reaction; this reaction does not need to add alkali and ligand, and the ideal ionic liquid can be obtained in a short time in the air atmosphere The reaction yield; the reaction system is non-corrosive to the equipment and has no special requirements on the reaction vessel, and the operation and post-treatment process of the catalytic system are relatively simple.

Description

technical field [0001] The invention belongs to the technical field of synthesis of dihydropyrimidinone compounds, and in particular relates to a method for promoting the synthesis of dihydropyrimidinone compounds by a dihydrogen phosphate ionic liquid under the conditions of no alkali, no ligand and no organic solvent. Background technique [0002] DHPMs have a variety of pharmacological activities and can be used as anticancer drugs or treatment of schizophrenia, which has attracted extensive attention of researchers. The traditional method of synthesizing dihydropyrimidin-4-one compound has: the condensation reaction of β-aminoamide and aldehyde (Dzhavakhishvili S G, Gorobets N Y, Shishkina S V, et al.Diversification of athieno[2,3-d]pyrimidin-4 -one scaffold via Regioselective Alkylation Reactions[J].Chem.2009,11(3),508-514.), reaction between methacrylate and amidines (Kunio I, Yoshiko K, YujiH J.Heterocyclic does the tube- compensation function of two modern mechanica...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/22B01J31/02
CPCB01J31/0279B01J31/0282B01J31/0284B01J31/0298C07D239/22
Inventor 朱安莲杜春燕陈玉娟李凌君
Owner HENAN NORMAL UNIV
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