Pyrazolo[3,4-d]pyrimidin-4(5H)-ketone derivative and preparation method and application thereof

A pyrazolo, 4-d technology, which is applied in the field of pyrazolo[3,4-d]pyrimidin-4-one derivatives and their preparation, can solve the problems of high production cost, high synthesis difficulty and the like, and achieves synthesis Low cost, simple preparation method and high herbicidal activity

Active Publication Date: 2018-09-04
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Compound A has good herbicidal activity and nematicide activity, but its pyrimidine ring contains two substituents, and the pyrimidine ring needs to be replaced many times during synthesis, which is difficult to synthesize and high in production cost

Method used

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  • Pyrazolo[3,4-d]pyrimidin-4(5H)-ketone derivative and preparation method and application thereof
  • Pyrazolo[3,4-d]pyrimidin-4(5H)-ketone derivative and preparation method and application thereof
  • Pyrazolo[3,4-d]pyrimidin-4(5H)-ketone derivative and preparation method and application thereof

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preparation example Construction

[0042] The present invention provides a method for preparing pyrazolo[3,4-d]pyrimidin-4(5H)-one derivatives described in the above scheme, comprising the following steps:

[0043] Under the action of an inorganic base, the compound having the structure shown in formula (a) is hydrolyzed in a protic solvent to obtain the compound having the structure shown in formula (b);

[0044]

[0045] The compound having the structure shown in formula (b) is subjected to acyl chloride reaction with chloride to obtain the compound having the structure shown in formula (c);

[0046]

[0047] Under the action of an acid-binding agent, a compound having a structure shown in formula (c) and a compound having a structure shown in formula (d) are subjected to a substitution reaction in methyl chloride to obtain a compound having a structure shown in formula (e);

[0048]

[0049] Under the action of an acid anhydride, the compound having the structure represented by formula (e) is conden...

Embodiment 1

[0106] Synthesis of 1-(3-fluorophenyl)-5-amino-1H-pyrazole-4-carboxylic acid (b1): In a 500mL round bottom flask, add 2.45g 1-(3-fluorophenyl)-5 -Amino-1H-pyrazole-4-carboxylic acid ethyl ester (a1), 4mL tetrahydrofuran, 12mL anhydrous methanol and 6mL 3mol / L sodium hydroxide aqueous solution, heated to reflux for 4 hours, removed most of the solvent under reduced pressure, and the residual liquid Acidify with 6mol / L hydrochloric acid to pH = 1, a milky white precipitate appears, filter, wash with water, and then wash with dichloromethane to remove unreacted ester, dry to obtain a white solid b1 (2.107g), yield 97%;

[0107] Synthesis of 1-(3-fluorophenyl)-5-amino-1H-pyrazole-4-formyl chloride (c1): In a 50mL round bottom flask, add 1.09g 1-(3-fluorophenyl)- 5-Amino-1H-pyrazole-4-carboxylic acid (b1), cooled in an ice bath and controlled at 0°C, add 10mL (molar ratio to the raw material is greater than 20) of thionyl chloride dropwise with a dropping funnel, after dropping, le...

Embodiment 2

[0115] The starting reactant was replaced by ethyl 1-tert-butyl-5-amino-1H-pyrazole-4-carboxylate (a2), and the reaction was carried out according to the steps in Example 1 to obtain product I2 (1.528g). The rate is 74.1%.

[0116] The resulting product is detected by nuclear magnetic resonance, and the obtained data are:

[0117] 1 H NMR (400MHz, CDCl 3 )δ:8.10(s,1H,Pyra-H),7.88(s,1H,CH),7.19(d,J=6.9Hz,1H,Ar-H),6.98(d,J=9.6Hz,1H, Ar-H),4.73(s,2H,CH 2 ),4.70(s,2H,CH 2 )2.30(t, J=2.3Hz, 2H, CH 2 ),1.81(s,9H,CH 3 ). 13 C NMR (101MHz, CDCl 3 )δ: 162.80, 156.71, 155.11, 152.62, 150.62, 146.59, 133.84, 124.95, 118.77, 115.94, 107.09, 106.42, 106.18, 76.63, 73.51, 67.50, 61.23, 30.422.29

[0118] According to the above data, the structure of product I2 can be obtained as:

[0119]

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Abstract

The invention provides a pyrazolo[3,4-d]pyrimidin-4(5H)-ketone derivative having the structure shown in the formula I. The derivative has a simple and novel structure, a preparation method is simple,raw materials are easily obtained, synthetic route is shorter, synthesis cost is low and industrial production is facilitated. The pyrazolo[3,4-d]pyrimidin-4(5H)-ketone derivative has high pre-emergence weeding activity and has selective inhibition on dicotyledonous plants. The embodiments show that the pyrazolo[3,4-d]pyrimidin-4(5H)-ketone derivative has better activity to rape, amaranth, barnyard grass and crabgrass at a dose of 1500g / ha, and shows 100% inhibition against amaranth and crabgrass. The formula (I) is shown in the description.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a pyrazolo[3,4-d]pyrimidin-4(5H)-one derivative and a preparation method thereof. Background technique [0002] Traditional pesticides have huge defects in terms of toxicity to animals and environmental protection. Therefore, the development trend of modern pesticides is to design and synthesize high-herbicidal active compounds that are green, efficient, and harmless to humans. The structure of pyrazolopyrimidine derivatives is similar to that of purine, and the existing herbicides of this kind have the characteristics of high efficiency, low toxicity, broad spectrum, long application period and safety to subsequent crops. [0003] Patent CA2484997 discloses a pyrazolo[3,4-d]pyrimidin-4(5H)-one compound A, which has the following structure: [0004] [0005] In the formula, [0006] Q is NO 2 , cyano, halogen, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P13/00
CPCA01N43/90C07D487/04
Inventor 李华斌李露阳郭丽慧李晓涵匡昕怡古建
Owner NANKAI UNIV
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