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4,6-dimethoxy-2-aminopyrimidine fatty acid derivative as well as preparation method and purpose thereof

A technology of fatty acid derivatives and aminopyrimidine, which is applied in the field of drug synthesis, can solve the problems of non-target organisms and environmental adverse effects, excessive pesticide residues, etc., and achieve good market development prospects, mild reaction conditions, and cheap and easy-to-obtain raw materials Effect

Inactive Publication Date: 2018-03-30
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The long-term use of large quantities of chemical pesticides has resulted in excessive pesticide residues, which have had many adverse effects on non-target organisms and the environment

Method used

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  • 4,6-dimethoxy-2-aminopyrimidine fatty acid derivative as well as preparation method and purpose thereof
  • 4,6-dimethoxy-2-aminopyrimidine fatty acid derivative as well as preparation method and purpose thereof
  • 4,6-dimethoxy-2-aminopyrimidine fatty acid derivative as well as preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of Ethyl-7-((4,6-dimethoxypyrimidine-2-)aminoheptanoate

[0047]

[0048] Add 155 mg (1 mmol) of 2-amino-4,6-dimethoxypyrimidine solid and 8 mL of dried DMF to a 50 mL pear-shaped bottle, stir to dissolve and add 2 g of anhydrous K 2 CO 3 , stirred at room temperature for 0.5h, then slowly added 194uL (1mmol) of ethyl 7-bromoheptanoate to the reaction system, stirred overnight at room temperature and monitored by TLC until the reaction was complete. After the reaction was completed, 40 mL of water was added thereto, and then extracted with 2×50 mL of ethyl acetate, and the combined organic phases were sequentially washed with 2×50 mL of 1N HCl solution and 2×50 mL of saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, then purified on a silica gel column, and eluted with petroleum ether / ethyl acetate (v / v, 6 / 1) to obtain a light yellow oily liquid with a yi...

Embodiment 2

[0050] Synthesis of o-tolyl 5-(4,6-dimethoxypyrimidine-2-)aminovaleric acid

[0051]

[0052] Add 155 mg (1 mmol) of 2-amino-4,6-dimethoxypyrimidine solid and 8 mL of dried DMF to a 50 mL pear-shaped bottle, stir to dissolve and add 2 g of anhydrous K 2 CO 3 , stirred at room temperature for 0.5 h, then slowly added 270 mg (1 mmol) of o-methylphenyl 5-bromopentanoate to the reaction system, stirred overnight at room temperature and monitored by TLC until the reaction was complete. After the reaction was completed, 40 mL of water was added thereto, followed by extraction with 2×50 mL of ethyl acetate, and the combined organic phases were successively washed with 2×50 mL of 1N HCl solution and 2×50 mL of saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, then purified on a silica gel column, and eluted with petroleum ether / ethyl acetate (v / v, 4 / 1) to obtain a light yellow oi...

Embodiment 3

[0054] Synthesis of 7-(4,6-dimethoxypyrimidine-2-)aminoheptanoic acid

[0055]

[0056] Weigh 311 mg of ethyl-7((4,6-dimethoxypyrimidine-2-)aminoheptanoate into a 50L pear-shaped bottle, add 10% hydrochloric acid solution and react at 60-80°C for 2-3 hours, and detect the reaction Completely, stop heating, after the reaction solution is cooled to room temperature.Extract 2 times with ethyl acetate, each 50mL, combine organic phase, decompression evaporate solvent, recrystallization in ethanol, yield 92%.1HNMR (CDCl3, 500Hz), δ: 1.30~1.45(m, 4H, CH2), 1.55~1.65(m, 4H, CH2), 2.28(t, J=7.5Hz, 3H, CH3), 3.37(q, J=6.5Hz, 2H, CH2), 3.82(s, 6H, OCH3), 5.36(s, 1H, Ar-H), 7.01(s, 1H, NH), 10.05(s, 1H, COOH).13C NMR(CDCl3, 125Hz) , δ: 24.55, 27.35, 28.64, 31.25, 35.03, 41.32, 54.38, 72.86, 158.09, 175.09, 178.04, .MS (ESI), m / z: 282 ([M+H]-).

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Abstract

The invention discloses 4,6-dimethoxy-2-aminopyrimidine fatty acid derivatives with the structure of formula I, the substituent R of which is selected from hydrogen; or selected from C1~C8 alkyl; or selected from cyano, halogen , phenyl, C1~C4 alkoxy, C1~C4 alkylthio substituted C1~C8 alkyl; or selected from phenyl; or selected from phenyl with 1 to 3 substituents, on the phenyl 1-3 substituents are selected from halogen, hydroxyl, carboxyl, nitro, cyano, phenyl, phenoxy, benzoyl, C1-C8 alkyl, C3-C8 cycloalkyl, C1-C4 alkoxy Group, C1~C4 haloalkyl, C1~C4 haloalkoxy, C1~C4 haloalkylthio, C1~C4 haloalkylsulfonyl. The synthetic route uses 4,6-dimethoxy-2-aminopyrimidine and fatty acid ester compounds as raw materials. This kind of compound has good antibacterial activity against various agricultural pathogenic fungi, and its target is dethiobiotin synthase in the biotin synthesis pathway.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and specifically relates to various 4,6-dimethoxy-2-aminopyrimidine fatty acid derivatives, their preferred preparation methods and their use as fungicides in plant disease control. Background technique [0002] The long-term use of large quantities of chemical pesticides has resulted in excessive pesticide residues, which have had many adverse effects on non-target organisms and the environment. With the enhancement of people's awareness of environmental protection and sustainable development, it has become a worldwide consensus to minimize the side effects of pesticides and to develop biologically rational pesticides. Biological pesticides (especially microbial and botanical pesticides) have the advantages of low toxicity, low residue, basically harmless to non-target organisms, and no pollution to the environment. The development and application of biological pesticides has gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/545A01N43/54A01P3/00
CPCC07D239/545A01N43/54
Inventor 姬志勤魏少鹏
Owner NORTHWEST A & F UNIV
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