Method for synthesizing all-carbon-substituted pyrimidine derivative

A technology for compounds and products, applied in the field of synthesizing all-carbon substituted pyrimidine derivatives, can solve the problems of high functionalization of raw materials and difficulty in obtaining

Inactive Publication Date: 2019-09-27
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Nevertheless, these methods still have some limitations, such as highly functionalized starting materials, difficult access, use of noble metal catalysts, etc.

Method used

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  • Method for synthesizing all-carbon-substituted pyrimidine derivative
  • Method for synthesizing all-carbon-substituted pyrimidine derivative
  • Method for synthesizing all-carbon-substituted pyrimidine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The synthesis of 2,6-bis(2-tolyl)-4-(2-ethoxyphenyl)pyrimidine-5-carboxylic acid ethyl ester (the structural formula of the compound is shown in formula IV-1), including the following steps:

[0024] Into the reaction tube, add 4-aminocoumarin (0.2 mmol), ammonium iodide (0.24 mmol), and solid benzaldehyde (0.6 mmol) successively, and use a double-row tube system to remove oxygen / refill argon and circulate three times. Dimethyl sulfoxide (0.2mmol, 18μL) and chlorobenzene (0.5mL) were sequentially injected through a syringe, and the tube was sealed and reacted at 150°C for 24h. The intermediate obtained from the reaction was cooled to room temperature, solid sodium hydroxide (0.48 mmol, 20 mg) and dimethyl sulfoxide (0.6 mL) were added, and stirred at room temperature (20-30°C) for 0.5 hours, and then bromoethane ( 0.48mmol, 52mg), and continue to stir for 3 hours. Treated with ethyl acetate and water, and separated by thin layer chromatography (petroleum ether / ethyl aceta...

Embodiment 2

[0028] In the synthesis of the compound represented by formula IV-2, 4-tolualdehyde replaces the benzaldehyde in Example 1, and other reaction conditions are the same as in Example 1, and the yield is 80%;

[0029]

[0030] White solid, m.p.140-142℃. 1 H NMR (400 MHz, CDCl 3 )δ8.49(d,J=8.2 Hz,2H), 7.65(d,J=8.1 Hz,2H), 7.54(dd,J=7.5,1.6 Hz,1H),7.40(td,J=8.3,1.7 Hz, 1H), 7.29–7.26 (m, 4H), 7.09 (t, J = 7.5 Hz, 1H), 6.93 (d, J = 8.3 Hz, 1H), 4.02–3.94 (m, 4H), 2.42 (s ,3H),2.41(s,3H),1.25(t,J=7.0 Hz,3H),0.87(t,J=7.1 Hz,3H). 13 C NMR(100MHz, CDCl 3 )δ167.7, 164.4, 164.2, 163.9, 156.0, 141.3, 139.8, 135.9, 134.7, 130.7, 129.2(2C), 129.0(2C), 128.8(2C), 128.7(2C), 128.2, 123.5, 120.7, 111.8, 64.1 ,61.1,21.6,21.4,14.5,13.4.

Embodiment 3

[0032] In the synthesis of the compound represented by formula IV-3, 4-fluorobenzaldehyde replaces the benzaldehyde in Example 1, and other reaction conditions are the same as in Example 1, and the yield is 82%;

[0033]

[0034] White solid, m.p.114-115℃. 1 H NMR (400 MHz, CDCl 3 )δ8.60(dd,J=8.4,5.9 Hz,2H),7.74(dd,J=8.5,5.4 Hz,2H),7.54(d,J=7.4 Hz,1H),7.42(t,J=7.8 Hz,1H),7.19–7.08(m,5H),6.94(d,J=8.3 Hz,1H),4.03–3.95(m,4H),1.26(t,J=7.0 Hz, 3H),0.89(t ,J=7.1 Hz,3H). 13 C NMR(101 MHz, CDCl 3 )δ167.4, 164.9 (J = 249.5 Hz), 163.9 (J = 258.5 Hz), 164.7, 163.4, 163.0, 155.9, 134.6 (J = 3.3 Hz), 133.3 (J = 2.8 Hz), 131.03, 130.9, 130.8, 130.7 ,130.72,127.76,123.71,120.76,115.5 (J = 21.5 Hz), 115.4 (J = 21.7 Hz), 111.7, 64.1, 61.3, 14.4, 13.4.

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Abstract

The invention discloses a method for synthesizing an all-carbon-substituted pyrimidine derivative, The method comprises the following steps: a 4-aminocoumarin compound, aromatic aldehyde and ammonium iodide react in chlorobenzene under oxidizing conditions to obtain an intermediate; the intermediate is mixed with base and a solvent to carry out basic hydrolysis, and an alkylating agent is added for O-alkylation to obtain a target product. The method of the invention has advantages of simple steps, easy availability of raw materials, no precious metal participation and the like, can overcome the disadvantage in the prior art that a substrate needs to be highly pre-functionalized, the reactants are easy to absorb moisture, the reaction requires precious metal catalysis, the steps are cumbersome and it is difficult to directly prepare an all-carbon-substituted pyrimidine derivative, and can play an important role in the research field of pyrimidine derivatives.

Description

Technical field [0001] The present invention relates to a method for synthesizing all-carbon substituted pyrimidine derivatives, specifically, it relates to a reaction of 4-aminocoumarin compounds, aromatic aldehydes, and ammonium iodide, followed by alkaline hydrolysis and O-alkane A method for preparing pyrimidine derivatives by radicalization. Background technique [0002] Multi-substituted pyrimidine derivatives are a kind of nitrogen-containing six-membered heterocyclic compounds with very important application value, which are widely used in natural products, medicine, agrochemicals, functional materials and other fields. Especially the special structure of pyrimidine itself makes it play an unparalleled role as a compound building block in organic catalytic synthesis, medicinal chemistry, coordination chemistry and supramolecular chemistry. Therefore, many chemical researchers have devoted themselves to the synthesis of pyrimidine derivatives and created a series of effec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/28
CPCC07D239/28
Inventor 李江胜陈晶杨盼盼谢欣芸姜思李志伟欧阳楚豪肖汀
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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