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Preparation method of N-2-pyridine-5-pyrimidine methylamine

A technology for pyrimidine methylamine and pyridine, which is applied in the field of preparation of N-2-pyridine-5-pyrimidine methylamine, can solve the problems of difficult to obtain, expensive sodium borohydride, low reduction yield of sodium borohydride and the like, and achieves a reduction in the The effect of high cost, high yield and low price

Inactive Publication Date: 2018-08-07
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patents WO2012092115 and WO 2013090547 report that 5-pyrimidine formaldehyde is used as a raw material, reacted with 2-aminopyrimidine, and then reduced by sodium borohydride to obtain N-2-pyridine-5-pyrimidinemethylamine. There are two disadvantages in this route. One is 5-pyrimidine formaldehyde is expensive and difficult to obtain. The second is to use expensive sodium borohydride, and the reduction yield of sodium borohydride is low

Method used

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  • Preparation method of N-2-pyridine-5-pyrimidine methylamine
  • Preparation method of N-2-pyridine-5-pyrimidine methylamine
  • Preparation method of N-2-pyridine-5-pyrimidine methylamine

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Embodiment 1

[0037] A preparation method of N-2-pyridine-5-pyrimidinemethylamine, comprising the steps of:

[0038] (1) Synthesis of 3-amino-2-methacrolein: 114g (1.0mol) 3-ethoxy-2-alkylacrolein was added to a 500ml reaction flask with a stirrer and a thermometer, and used in ice / Cool with brine, add 750ml of 25% ammonia water dropwise at 0-10°C, dropwise for 1-2 hours, after the dropwise addition, slowly heat up to 25°C, the solution is yellow, continue to react for 2-3 hours; then concentrate the reaction under reduced pressure The mixture, 3-aminoacrolein crystals precipitated, was recrystallized from ethyl acetate to obtain 76.5 solids, the yield was 90%, and the melting point was 113-114°C;

[0039] (2) Synthesis of 5-methylpyrimidine: Add 85.0g (1.0mol) 3-amino-2-alkylacrolein, 54g (1.2mol) formamide and 2.0g piperidine acetate with a stirrer, reflux Put the condenser tube and thermometer in a 500ml reaction bottle, raise the temperature to 125°C, continue the reaction for 12-14h;...

Embodiment 2

[0043] A preparation method of N-2-pyridine-5-pyrimidinemethylamine, comprising the steps of:

[0044] (1) with embodiment 1;

[0045] (2) with embodiment 1;

[0046](3) Synthesis of 5-bromomethylpyrimine: Dissolve 94.0g (1.0mol) of 5-methylpyridine in 500ml of carbon tetrachloride solution, add 2.g of 2,2-azoisobutyronitrile, heat Reflux, then add bromine 176g (1.1mol) dropwise, and continue the reaction for 2-4 hours after the addition; then cool to room temperature, filter, and the filtrate is washed with aqueous sodium sulfite, dried over magnesium sulfate, and concentrated. Distilled under reduced pressure, collected 65-66 ° C / 10mmHg fraction 111.8g, yield 65%, 1H NMR (CDCl3): δ4.40 (s, 2H), 8.79 (s, 2H), 9.16 (s, 1H).

[0047] (4) Synthesis of N-2-pyridine-5 pyrimidinemethylamine Synthesis: in 500mL equipped with stirrer, thermometer, condenser tube

[0048] In a four-necked reaction flask, add 137.6g (0.8mol) of 5-bromomethylpyrimidine, 77.1g (0.82mol) of 2-aminopy...

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Abstract

The invention belongs to the technical field of pesticide intermediate preparation, and more specifically relates to a preparation method of N-2-pyridine-5-pyrimidine methylamine. According to the reparation method, cheap and easily available 3-ethoxy-2-methylacrolein is taken as an initial raw material, and is reacted with 25% ammoniacal liquor so as to obtain 3-amino-2-methylacrolein; 3-amino-2-methylacrolein and methanamide are subjected to cyclization so as to obtain 5-methylpyrimidine; in a carbon tetrachloride solution, N-bromosuccinimide is adopted for bromination so as to obtain 5-bromo methylpyrimidine; under the action of triethylamine, 5-bromo methylpyrimidine is reacted with 2-aminopyridine so as to obtain N-2-pyridine-5-pyrimidine methylamine. In the novel N-2-pyridine-5-pyrimidine methylamine preparation process, 3-ethoxy-2-methylacrolein is taken as the initial raw material, ammoniation, cyclization, and bromination are adopted to obtain 5-bromo methylpyrimidine, and 5-bromo methylpyrimidine is reacted with 2-aminopyridine so as to obtain the target product. According to the preparation method, cheap and easily available 3-ethoxy acrolein is adopted, so that production cost is reduced greatly compared with that of routine technology wherein expensive 5-pyrimidine carbaldehyde is adopted.

Description

technical field [0001] The invention belongs to the technical field of preparation of pesticide intermediates, and in particular relates to a preparation method of N-2-pyridine-5-pyrimidinemethylamine. Background technique [0002] Triflumezopyrim (triflumezopyrim) chemical name: 2-hydroxy-4-oxo-1-5-pyrimidinylmethyl-3-[3-(trifluoromethyl)phenyl]-4H-, chemical structural formula is: [0003] [0004] Triflumezopyrim (triflumezopyrim) is a new type of mesoionic or zwitterionic insecticides (mesoionic insecticides; zwitterionic insecticides) developed by DuPont, and it is also a new type of pyrimidinone compound. It has high efficiency, long-lasting effect, low dosage, and is environmentally friendly. It mainly controls rice planthoppers and leafhoppers, and has good control effects on various pests such as Lepidoptera and Homoptera. It can be used for cotton, rice, Crops such as corn and soybeans. [0005] Synthesis of trifluoropyrimidine from N-2-pyridine-5-pyrimidineme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 刘安昌汪鲁焱郑怡倩黄时祥包洋
Owner WUHAN INSTITUTE OF TECHNOLOGY
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