Substituted five-membered heterocyclic compound containing pyrimidine rings and preparation method and application thereof

A technology for five-membered heterocycles and compounds, which is applied to the field of substituted five-membered heterocycles containing pyrimido rings and the preparation thereof, and can solve the problems of very different structures and the like.

Active Publication Date: 2018-05-25
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, its structure is far from the structure of the pyrimido ring-containing substituted five-membered heterocyclic compound shown in the general formula I of the present invention, and has no report with the compound shown in the general formula I of the present invention

Method used

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  • Substituted five-membered heterocyclic compound containing pyrimidine rings and preparation method and application thereof
  • Substituted five-membered heterocyclic compound containing pyrimidine rings and preparation method and application thereof
  • Substituted five-membered heterocyclic compound containing pyrimidine rings and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0335] Embodiment 1: Preparation of intermediate 2-((3-methylisoxazolo[5,4-d]pyrimidin-4-yl)amino)ethanol

[0336] 1) Preparation of 5-amino-3-methylisoxazole-4-cyano

[0337]

[0338] Dissolve 14g (0.2 mol) of hydroxylamine hydrochloride in 80mL of 10% sodium hydroxide, add 27.2g (0.2 mol) of (1-ethoxyethylene) malononitrile, add a small amount of ice to keep the temperature below 50°C, and continue at room temperature After stirring for 1.5 hours, the solid was filtered, washed with water, and recrystallized from absolute ethanol to obtain 16.5 g of a solid product.

[0339] 2) Preparation of 4-chloro-3-methylisoxazolo[5,4-d]pyrimidine

[0340]

[0341] Phosphorus oxychloride (POCl 3 ) 40mL and N,N-dimethylformamide 1mL were added to the reaction flask, stirred at room temperature for 1 hour, added 5-amino-3-methylisoxazole-4-cyano group (451mg, 3.66mmol), and heated to React at 160°C for 15-36 hours, and distill the reaction solution under reduced pressure to obtai...

Embodiment 2

[0342] Embodiment 2: Synthesis of intermediate 2-(1-(4-chlorophenyl)-1H-pyrazole-3-oxyl)ethylamine hydrochloride

[0343] 1) Preparation of N-Boc-2-bromoethylamine

[0344]

[0345] Put 20.5g (0.1mol) of bromoethylamine bromate in 80ml of tetrahydrofuran, add 10.08g (0.12mol) of sodium bicarbonate and 50ml of water in sequence, and add 21.80g (0.1mol) of di-tert-butyl dicarbonate dropwise under stirring at room temperature Ester, after dropping, continue to react for 4-10 hours. After the reaction was completed, the solvent was evaporated under reduced pressure, and (3×50ml) ethyl acetate was added for extraction. The organic phase was washed with 50ml of saturated brine, and 21.84g of a colorless oily liquid was obtained after precipitation, with a yield of 97.5%.

[0346] 2) Preparation of N-Boc-2-(1-(2-chlorophenyl)-1H-pyrazole-3-oxyl)ethylamine

[0347]

[0348] Mix 2.24g (0.01mol) N-Boc-2-bromoethylamine with 1.94g (0.01mol) 1-(4-chlorophenyl)-1H-3-hydroxypyrazole...

Embodiment 3

[0352] Embodiment 3: the preparation of compound 21-180

[0353]

[0354] 0.17g (0.001mol) of 4-chloro-3-methylisoxazolo[5,4-d]pyrimidine and 0.27g (0.001mol) of 2-(1-(4-chlorophenyl)-1H-pyridine Azole-3-oxy)ethylamine hydrochloride was added to 50ml of toluene. Add 0.45g (0.002mol) triethylamine, heat to reflux, and react for 4-10 hours. After the reaction is monitored by TLC, evaporate the solvent under reduced pressure, add (3×30ml) ethyl acetate for extraction, and use saturated brine for the organic phase After washing with 50ml, the residue was subjected to column chromatography (eluent: ethyl acetate and petroleum ether (boiling range: 60-90°C), volume ratio: 1:4) to obtain 0.27g of a white solid. The melting point is 156.5°C.

[0355] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3)δ(ppm):2.46(3H,s),4.06-4.12(2H,q),4.55-4.58(2H,t),5.93(1H,d),5.94(2H,m),7.37(2H,dd ), 7.51(2H,dd), 7.72(1H,d), 8.51(1H,s).

[0356] Other compounds of the present invention c...

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Abstract

The invention discloses a substituted five-membered heterocyclic compound containing pyrimidine rings. The structure is shown in a formula I: (the formula I is shown in the description), and the definition of each substation group is shown in the description. The substituted six-membered heterocyclic compound has the advantages that the broad-spectrum bacteria-killing and insect-killing activity is realized; the good preventing and controlling effect is realized for cucumber downy mildew, wheat powdery mildew, puccinia polysora, rice blast, cucumber anthracnose and the like.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, and specifically relates to a novel substituted five-membered heterocyclic compound containing a pyrimido ring, a preparation method and application thereof. Background technique [0002] Patent JP 59036683 A discloses the application of pyrazole or isoxazolopyrimidine compounds represented by the following general formula as agricultural acaricides. [0003] [0004] However, its structure is far from the structure of the pyrimido ring-containing substituted five-membered heterocyclic compound represented by the general formula I of the present invention, and has not been reported with the compound represented by the general formula I of the present invention. Contents of the invention [0005] The object of the present invention is to provide a pyrimido ring-containing substituted five-membered heterocyclic compound that can control various germs, pests and mites, and its preparation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04C07D487/04A01N43/90A01P1/00A01P3/00A01P7/02A01P7/04
CPCA01N43/90C07D487/04C07D498/04
Inventor 李淼杨吉春李志念杨帆孙芹孙金强孙庚刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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