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Preparation method of pyridodipyrimidine and pyridodipyrazole derivatives

A technology for pyridodipyrazole and derivatives, which is applied in the field of synthesis of pyridodipyrimidine derivatives and pyridodipyrazole derivatives, can solve problems such as unfavorable industrial production, high reaction temperature, complicated procedures, etc. Low cost, high reaction efficiency, good safety effect

Inactive Publication Date: 2020-02-14
YANTAI UNIV
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  • Abstract
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  • Application Information

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Problems solved by technology

[0019] The disadvantage of this method is that the reaction is carried out in two steps, the required steps are more, the procedure is cumbersome, and the reaction temperature is higher, which is not conducive to industrial production.

Method used

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  • Preparation method of pyridodipyrimidine and pyridodipyrazole derivatives
  • Preparation method of pyridodipyrimidine and pyridodipyrazole derivatives
  • Preparation method of pyridodipyrimidine and pyridodipyrazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis:

[0058] The reaction formula is:

[0059]

[0060] The specific steps are: add 0.3mmol 6-bromo-2-methylquinoline, 0.66mmol 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, 0.45 mmol I 2 , 2mLDMSO, and the reaction mixture was stirred at 110° C. for 6 hours in an air environment, and the reaction solution was extracted with ethyl acetate, and the organic layer was washed with 10% sodium thiosulfate solution (w / w), dried over anhydrous sodium sulfate, Concentrate under reduced pressure and dry in vacuo to get the crude product, use ethyl acetate / petroleum ether=2:1 (V / V) as the eluent for column separation and purification of the crude product to get the desired product, the product is a white solid, the yield was 86%.

[0061] The NMR result of gained product is: 1 H NMR (400MHz, CDCl 3 )δ8.16(dd, J=8.9,0.7Hz,1H),8.06(d,J=2.5Hz,1H),7.88-7.82(dt,J=8.9,0.7Hz,1H),7.75(dd,J =9.0, 2.3Hz, 1H), 7.41(d, J=8.6Hz, 1H), 3.78(s, 6H), 3.24(s, 6H). 13 C NMR (10...

Embodiment 2

[0063] Synthesis:

[0064] The reaction formula is:

[0065]

[0066] The specific steps are: add 0.3mmol 7-chloro-2-methylquinoline, 0.66mmol 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, 0.45 mmol I 2 , 2mL DMSO, the reaction mixture was stirred at 110°C for 6 hours in air, and the reaction solution was extracted with ethyl acetate, the organic layer was washed with 10% sodium thiosulfate solution (w / w), dried over anhydrous sodium sulfate , concentrated under reduced pressure and vacuum dried to obtain the crude product, the crude product was separated and purified by column separation and purification with ethyl acetate / petroleum ether=2:1 (V / V) as the eluent to obtain the desired product, the product was a white solid, and The rate is 78%.

[0067] The NMR result of gained product is: 1 H NMR (400MHz, CDCl 3 )δ8.23(dd, J=8.7,1.0Hz,1H),7.99(d,J=2.4,1H),7.84(d,J=8.8Hz,1H),7.51(dd,J=8.8,2.2Hz , 1H), 7.40(d, J=8.5Hz, 1H), 3.78(s, 6H), 3.25(s, 6H). 13 C NMR (100...

Embodiment 3

[0069] Synthesis:

[0070] The reaction formula is:

[0071]

[0072] The specific steps are: add 0.3mmol 6-chloro-2-methylquinoline, 0.66mmol 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, 0.45 mmol I 2 , 2mLDMSO, and the reaction mixture was stirred at 110° C. for 10 hours in an air environment, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with 10% sodium thiosulfate solution (w / w), and dried over anhydrous sodium sulfate. Concentrate under reduced pressure and dry in vacuo to get the crude product, use ethyl acetate / petroleum ether=1:2 (V / V) as the eluent for column separation and purification to get the desired product, the product is a white solid, the yield was 52%.

[0073] The NMR result of gained product is: 1 H NMR (400MHz, CDCl 3 )δ8.17(m,1H),7.92(d,J=9.0Hz,1H),7.88(d,J=2.6Hz,1H),7.62(dd,J=9.0,2.5Hz,1H),7.42( d,J=8.6Hz,1H),3.78(s,6H),3.24(s,6H). 13 C NMR (100MHz, CDCl 3 )δ159.14, 157.20, 156.60, 153.67, 150....

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Abstract

The invention discloses a preparation method of pyridodipyrimidine and pyridodipyrazole derivatives. The method comprises the following steps: carrying out a contact reaction on substituted methylquinoline derivatives, 6-amino-1,3-dimethylpyrimidine-2,4-dione or 3-methyl-1-phenyl-5-aminopyrazole and an iodine elementary substance to synthesize pyridodipyrimidine compounds, pyridodipyrazole compounds and derivatives thereof in one-pot. According to the preparation method, the adopted raw materials are cheap and easy to obtain, the preparation method is simple, steps are relatively short, the yield is up to 97%, and a feasible method is provided for industrially preparing the compounds.

Description

technical field [0001] The invention relates to a synthesis method of pyridobipyrimidine derivatives and pyridobipyrazole derivatives, and belongs to the technical field of organic and pharmaceutical synthesis. [0002] technical background [0003] Pyridopyrimidine compounds have attracted extensive attention in recent years. Their derivatives are known to have significant pharmacological activity, and relevant studies have fully demonstrated their tyrosine effects on epidermal growth factor receptor, 5-phosphoribosyl-1-pyrophosphate synthase 2 and dihydrofolate reductase 3 The acid kinase domain has potent inhibitory properties. Numerous reports describe the antitumor, antiviral, antioxidant, antifungal, and hepatoprotective effects of these compounds. [0004] In order to prepare these complex molecules, a large number of scientific researchers have been working on the synthesis of such compounds. Consequently, numerous reports have emerged in the literature, and the me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14C07D519/00
CPCC07D471/14C07D519/00
Inventor 祝艳平解镕基邵天麒宋利群刘凯璇张秋伊杨义杰孙媛媛
Owner YANTAI UNIV
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