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Synthetic method of difluoroalkyl substituted uracil, uridine or uridylic acid

A technology of difluoroalkyl and synthetic methods, which is applied in the synthesis of uridine or uridine acid, and in the field of uracil, to achieve the effects of short reaction steps, accelerated reaction, simple and easy-to-obtain raw materials and reagents

Inactive Publication Date: 2016-04-20
ZUNYI MEDICAL UNIVERSITY
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  • Abstract
  • Description
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Problems solved by technology

[0004] The present invention intends to provide a method for synthesizing difluoroalkyl substituted uracil, uridine or uridine acid, so as to solve the problem that the prior art cannot synthesize difluoroalkyl substituted uracil, uridine, uridine efficiently and concisely. Disadvantages of the method of glycosides and their derivatives

Method used

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  • Synthetic method of difluoroalkyl substituted uracil, uridine or uridylic acid
  • Synthetic method of difluoroalkyl substituted uracil, uridine or uridylic acid
  • Synthetic method of difluoroalkyl substituted uracil, uridine or uridylic acid

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preparation example Construction

[0027] The invention provides a method for synthesizing difluoroalkyl substituted uracil, uridine or uridine acid. Preferably, the method includes the step of: in an inert solvent, at a certain temperature (such as 0°C-100°C; preferably 10°C-60°C), under the irradiation of blue light or green light in visible light, the iridium-containing , the complex of ruthenium is a photocatalyst, and the compound of formula A (ie uracil, uridine, uridine acid or its derivatives) is reacted with the compound of formula B) for a period of time (such as 1-36 hours) to form the compound of formula C (difluoroalkyl substituted uracil, uridine, uridine acid and its derivatives);

[0028]

[0029] In various forms, R 1 , R 2 , R 3 , R 4 , X is defined as mentioned above.

[0030] More preferably, the compound of formula A is a compound selected from the group consisting of:

[0031]

[0032] Wherein, the compound of formula B is preferably a compound selected from the following group...

Embodiment 1

[0049]

[0050] To a 25mL reaction tube, add 2.6mg (1mol%) Ir(PPy) 3 , Na 2 CO 3 (0.8mmol), compound A-1 (0.4mmol, 1 equivalent), after nitrogen replacement three times, add 2mL dimethylsulfoxide (DMSO), inject 100μL (0.80mmol) compound B-1, stir under blue light irradiation for 12 hours , to obtain compound C-1 with a yield of 92%. 1 HNMR (400MHz, CDCl 3 )δ7.66(s, 1H), 4.34(q, J=7.2Hz, 2H), 3.47(s, 3H), 3.30(s, 3H), 1.33(t, J=7.2Hz, 3H). 19 FNMR (376MHz, CDCl 3 ) δ 104.9 (s, 2F).

Embodiment 2

[0052]

[0053] To a 25mL reaction tube, add 2.6mg (1mol%) Ir(PPy) 3 , k 2 HPO 4 (0.8mmol), compound A-1 (0.4mmol, 1 equivalent), after nitrogen replacement three times, add 2mL dimethylsulfoxide (DMSO), inject 100μL (0.80mmol) compound B-1, stir under blue light irradiation for 12 hours , to obtain compound C-1 with a yield of 98%. 1 HNMR (400MHz, CDCl 3 )δ7.66(s, 1H), 4.34(q, J=7.2Hz, 2H), 3.47(s, 3H), 3.30(s, 3H), 1.33(t, J=7.2Hz, 3H). 19 FNMR (376MHz, CDCl 3 ) δ 104.9 (s, 2F).

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Abstract

The invention discloses a synthetic method of difluoroalkyl substituted uracil, uridine or uridylic acid under a simple and convenient condition. To be specific, simple uracil, uridine or uridylic acid and a halogenated difluoroalkyl compound (chloro, bromo, iodo) are taken as the starting point, and under visible light irradiation, a coordination compound taking iridium and ruthenium as the core is taken as a catalyst, so that the method of obtaining various difluoroalkyl substituted uracil, uridine, uridylic acid and derivatives thereof at the high yield is achieved. According to the synthetic method, the simple and easily available uracil, uridine, uridylic acid, derivatives thereof and the halogenated difluoroalkyl compound (chloro, bromo, iodo) are taken as the raw materials, the advantages that the dosage of the catalyst is small, the application range of the substrate is wide, the operation is simple and convenient, the reaction efficiency is high and the like are achieved; besides, as the obtained structures are similar structures of marketing drugs at present, and are building blocks of novel nucleic acid molecules at the same time, a larger application prospect in the field of biological medicines is achieved.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing difluoroalkyl substituted uracil, uridine or uridine acid. Background technique [0002] Uracil and uridine are one of the base components in RNA. At the same time, it is also the core structure of some antiviral and antitumor drugs (such as: fluorouracil, zidovudine, stavudine, deoxyfluorouracil, carmofur, etc.). On the other hand, difluoroalkyl, as an important building block, has very important applications in the field of biomedicine. However, it is very rare to introduce a difluoroalkyl group into uracil by currently known methods, and it is usually realized by protecting uracil in the presence of copper salt or peroxide (Chemical Communications, 50(44) , 5887-5890, 2014; Tetrahedron, 67(12), 2323-2331; 2011) These methods not only have low yield (<60%) but also have poor functional group compatibility, and need to protect the amino and hydroxy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54C07D239/545C07D239/557C07H19/067C07H19/073C07H19/10C07H1/00
CPCC07D239/54C07D239/545C07D239/557C07H1/00C07H19/067C07H19/073C07H19/10
Inventor 贺春阳张新刚李晓飞
Owner ZUNYI MEDICAL UNIVERSITY
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