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Method for preparing 5-sulfur/selenium-modified uracil derivative

A technology of uracil derivatives and uracil, which is applied in organic chemistry and other fields, and can solve problems such as limited applications

Active Publication Date: 2019-04-19
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction requires transition metal catalysis and the presence of a strong base, which greatly limits the application of the reaction

Method used

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  • Method for preparing 5-sulfur/selenium-modified uracil derivative
  • Method for preparing 5-sulfur/selenium-modified uracil derivative
  • Method for preparing 5-sulfur/selenium-modified uracil derivative

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Experimental program
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Effect test

preparation example Construction

[0037] The preparation of diselenide refers to the synthetic method of literature: add aryl boronic acid (4.0mmol), elemental selenium (12.0mmol), silver nitrate (0.8mmol), dimethyl sulfoxide (DMSO, 20mL) into the reaction tube, Stir at 120°C, monitor the progress of the reaction by thin layer chromatography, the reaction is complete after about 2 hours. 200 mL of water and 100 mL of ethyl acetate were added to the resulting mixture for extraction, the organic phases were combined and then dried by adding anhydrous sodium sulfate, concentrated and separated by column chromatography to obtain the product.

[0038] The reaction equation is as follows:

[0039]

[0040] R is a benzene ring, a naphthalene ring, a heterocycle or a substituted benzene ring.

Embodiment 1

[0046] Add 0.2mmol uracil, 0.1mmol NaI and a stirring bar to a clean Schlenk reaction tube, then add 3ml DMSO solvent with a syringe, and finally add 0.3mmol thiophenol and 1.8mmol H with a micro syringe 2 o 2 (adding in three times at intervals of 3 hours), reacted at 100°C for 15 hours, and detected by TLC spot plate; 5-phenylthiouracil, light yellow solid, yield 90%. The structural formula of the product and its characterization data are as follows:

[0047]

[0048] 1 H NMR (500MHz, DMSO-d 6 )δ11.40(s, 2H), 7.92(s, 1H), 7.28(t, J=7.7Hz, 2H), 7.16(dd, J=14.2, 7.3Hz, 3H).

[0049] 13 C NMR (126MHz, DMSO-d 6 )δ162.80, 151.74, 149.50, 137.26, 129.44, 126.72, 125.98, 102.37.

[0050] LC-MS (ESI) calcd for C 10 h 7 N 2 o 2 S(M-H) - :219.02, Found 219.02.

Embodiment 2

[0052] Add 0.2mmol uracil, 0.1mmol NaI and 0.3mmol p-cresol and a stir bar to a clean Schlenk reaction tube, then add 3mL DMSO solvent with a syringe, and finally add 1.8mmol H with a micro syringe 2 o 2 (3 hours at intervals, added in three times), reacted at 100°C for 15 hours, TLC plate detection: after the reaction was completed, the reaction solution was added with water and extracted with ethyl acetate for 3 times, and the organic layer was concentrated and separated by column chromatography to obtain pure 5- p-tolylthiouracil, white solid, yield 92%. The structural formula of the product and its characterization data are as follows:

[0053]

[0054] 1 H NMR (500MHz, DMSO-d 6 )δ11.37(s,1H),11.33(d,J=4.6Hz,1H),7.85(d,J=5.8Hz,1H),7.10(s,4H),2.24(s,3H).

[0055] 13 C NMR (126MHz, DMSO-d 6 )δ162.30, 151.28, 148.21, 135.18, 132.87, 129.61, 127.09, 102.89, 20.48.

[0056] LC-MS (ESI) calcd for C 11 h 9 N 2 o 2 S(M-H) - :233.03,Found 233.03.

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Abstract

The invention belongs to the field of organic chemistry and particularly relates to a method for efficiently preparing a 5-sulfur / selenium-modified uracil derivative. The method comprises the steps ofenabling a thiophenol compound shown as a formula I or a diselenide ether compound shown as a formula II to react with uracil shown as a formula III in a solvent in the presence of an iodine source and an oxidant to obtain the 5-sulfur-modified uracil derivative shown as a formula IV or the 5-selenium-modified uracil derivative shown as a formula V. The provided general method for preparing the sulfur / selenium-modified uracil compound through a one-step approach without metal catalysis and pre-functionalization is environmentally friendly, simple and feasible, raw materials are simple and areeasily obtained, the range of substrates is wide, and the application prospect is broad.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for preparing 5-sulfur / selenium modified uracil derivatives. Background technique [0002] 5-Alkyl or 5-alkaryl modified pyrimidine derivatives are important intermediates for the synthesis of antiviral agents. Schinazi's group reported several 5-(phenylenyl)pyrimidine nucleosides with good biological activity and It is pointed out that it can be used as a potential antiviral drug (J.Med.Chem.1986,29,1293), and its inhibitory activity to dihydrouracil dehydrogenase and uridine phosphorylase is revealed (J.Med.Chem. 1986, 36, 4250). But the preparation of 5-alkyl or 5-alkaryl substituted pyrimidine derivatives is a very difficult problem. [0003] In 1979, Anzai's research group first reported the preparation of 5-sulfur / selenium modified uracil derivatives with sulfuryl chloride and diphenyl disulfide / diselenide. The reaction equation is as figure 1 shown...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/60C07D409/12C07D239/545
CPCC07D239/545C07D239/60C07D409/12
Inventor 程靓李学东刘利
Owner INST OF CHEM CHINESE ACAD OF SCI