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Pyrimidine-containing fused heterocyclic compounds, and preparation method and application thereof

A compound and cyclic technology, applied in the field of pyrimidocyclic compounds and their preparation, can solve the problems such as unreported structural pyrimidocyclic compounds

Active Publication Date: 2020-04-07
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, the pyrimido ring-containing compound with the structure shown in the general formula I of the present invention has not been reported

Method used

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  • Pyrimidine-containing fused heterocyclic compounds, and preparation method and application thereof
  • Pyrimidine-containing fused heterocyclic compounds, and preparation method and application thereof
  • Pyrimidine-containing fused heterocyclic compounds, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0266] Embodiment 1: Preparation of intermediate 2-((3-methylisoxazolo[5,4-d]pyrimidin-4-yl)amino)ethanol

[0267] 1) Preparation of 5-amino-3-methylisoxazole-4-cyano

[0268]

[0269] 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.

[0270] 2) Preparation of 4-chloro-3-methylisoxazolo[5,4-d]pyrimidine

[0271]

[0272] 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

[0276] Embodiment 2: the preparation of compound 7-1

[0277]

[0278] 0.54 g (2 mmol) of 4-(2-((3-methylisoxazolo[5,4-d]pyrimidin-4-yl)amino)ethyl)phenol and 0.25 g (2 mmol) of benzyl chloride were added Add 0.41g (3mmol) of potassium carbonate to 5ml of N,N-dimethylformamide, heat to 80°C, and react for 4-10 hours. After the reaction is monitored by TLC, pour the reaction solution into 50ml of saturated saline, Extraction was carried out in three portions with 100 ml of ethyl acetate and dried. After precipitation, the product was purified by column chromatography to obtain 0.45 g of the product, namely compound 7-1, with a melting point of 123.0°C.

[0279] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):8.50(s,1H),7.35-7.42(m,5H),7.15(d,2H),6.97(d,1H),5.16(s,1H),5.07(s,2H), 3.87(q,2H), 2.93(t,2H), 2.37(s,3H).

Embodiment 3

[0280] Embodiment 3: the preparation of compound 31-33

[0281]

[0282] Add 0.16 g of 60% sodium hydride into the reaction flask, wash with petroleum ether, add 5 ml of N,N-dimethylformamide, and then add 4-(2-((3-methylisoxazolo[ 5,4-d]pyrimidin-4-yl)amino)ethyl)phenol 0.54g (2mmol), after stirring at room temperature for 2 minutes, add intermediate 2,3-dichloro-5-trifluoromethylpyridine 0.43g (2mmol ), stirred and reacted at 60°C for 2 hours. After the reaction was monitored by TLC, the reaction solution was poured into 50 ml of saturated brine, extracted three times with 100 ml of ethyl acetate, and dried. After precipitation, 0.58 g of the product was purified by column chromatography, namely compound 31-33. The melting point is 141.7°C.

[0283] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):8.53(s,1H),8.25(s,1H),7.99(s,1H),7.32(d,2H),7.16(d,2H),5.25(s,1H),3.96( q,2H), 3.05(t,2H), 2.48(s,3H).

[0284] Other compounds of the present invention can...

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Abstract

The invention discloses pyrimidine-containing fused heterocyclic compounds, and a preparation method and application thereof. The structures of the pyrimidine-containing fused heterocyclic compounds are as shown in a general formula I which is described in the specification. In the general formula I, each substituent group is as defined in the specification. The compounds provided by the inventionhave broad-spectrum bactericidal activity, and have excellent prevention and treatment effects on cucumber downy mildew, wheat powdery mildew and the like.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, and in particular relates to a novel pyrimidocyclic compound and its preparation method and application. Background technique [0002] The article Pest Management Science (2008), 64(12), 1267-1277 announced the application of isoxazolopyrimidine compounds shown in the following structures as agricultural fungicides. [0003] [0004] However, there are no reports of compounds containing pyrimido rings with structures as shown in the general formula I of the present invention. Contents of the invention [0005] The object of the present invention is to provide a compound containing pyrimido ring which can control various germs, its preparation method and its use in the preparation of medicines for preventing and controlling germs in agriculture or other fields. [0006] To achieve the above object, the technical scheme of the present invention is as follows: [0007] A compound contai...

Claims

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Application Information

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IPC IPC(8): C07D498/04C07D487/04A01N43/90A01P3/00
CPCC07D498/04C07D487/04A01N43/90
Inventor 李淼杨吉春孙芹吴峤兰杰刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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