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Preparation method for 5-bromouracil

A technology for bromouracil and uracil, applied in the field of drug synthesis, can solve the problems of large environmental pollution, low uracil yield, troublesome post-processing and the like, and achieve the effects of simple post-processing, high yield and good yield

Active Publication Date: 2015-12-02
日照新睿招商发展有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] These methods have some disadvantages: need to use high boiling point and highly toxic solvents, post-processing is very troublesome and pollutes the environment; some reactions require expensive bromination reagents and catalysts, and there are also literatures that try to use more environmentally friendly KBr-H 2 o 2 -The system of catalase carries out bromination, but the yield of uracil is very low, only 4% (Bulletin of the Chemical Society of Japan, 1989, 62 (11), 3750-3751)

Method used

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  • Preparation method for 5-bromouracil
  • Preparation method for 5-bromouracil
  • Preparation method for 5-bromouracil

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Add 45ml of hydrochloric acid (6mol / L), 10g of uracil (89mmol) and 18.4g of NaBr (178mmol) into a 250mL three-neck flask, heat and stir at 50°C for half an hour, then cool to room temperature, and stir rapidly Add 54mL of NaClO (2mol / L) aqueous solution dropwise, react at room temperature for 3 hours after the addition is complete, and monitor the reaction end point with a sample. After the reaction, use starch potassium iodide test paper to detect whether there is NaClO in the reaction solution. Sodium sulfosulfate removes excess NaClO. Then adjust the pH value to about 8-9 with 6mol / L NaOH to obtain a white solid, filter it with suction and wash once with ice ethanol to obtain 15.6 g of 5-bromouracil with a yield of 91.5%.

[0035] Product confirmation: the liquid chromatogram and NMR spectrum of the prepared product are as follows: figure 1 , figure 2 shown.

[0036] Replacement examples 1-1 to 1-7:

[0037] The preparation method is the same as in Example 1, th...

Embodiment 2

[0043] Add 12ml of acetic acid, 10g of uracil (89mmol) and 18.4g of NaBr (178mmol) into a 250mL three-neck flask, heat and stir at room temperature for half an hour, then add dropwise 54mL of NaClO (2mol / L) aqueous solution under rapid stirring, After the addition, react at room temperature for 3 hours, and monitor the end point of the reaction with a sample. After the reaction, use starch potassium iodide test paper to detect whether there is NaClO in the reaction solution. If so, remove excess NaClO with saturated sodium thiosulfate. Then adjust the pH value to about 8-9 with NaOH to obtain a white solid, which was filtered by suction and washed once with ice ethanol to obtain 15.1 g of 5-bromouracil with a yield of 88.6%.

Embodiment 3

[0045] Mix 10g of uracil (89mmol) and 5mL of water in a 250mL three-necked flask, add 21ml of concentrated sulfuric acid dropwise under stirring, stir for 5‐10 minutes after the drop is complete, then add 18.4g of NaBr (178mmol), and then stir rapidly Add 54mL of NaClO (2mol / L) aqueous solution dropwise, react at room temperature for 3 hours after the addition is complete, and monitor the reaction end point with a sample. After the reaction, use starch potassium iodide test paper to detect whether there is NaClO in the reaction solution. Sodium sulfosulfate removes excess NaClO. Then adjust the pH value to about 8-9 with 6M NaOH to obtain a white solid, filter it with suction, and wash once with ice ethanol to obtain 16.2 g of 5-bromouracil with a yield of 95.1%.

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Abstract

The invention discloses a preparation method for 5-bromouracil. By taking uracil as an initial raw material, sodium bromide and sodium hypochlorite as a green bromating agent, and water as a solvent, a mild brominating reaction is carried out under an acidic condition to obtain a high purity target product. The preparation method disclosed by the invention is green and environmental-friendly in synthetic process, convenient in post-treatment and suitable for large-scaled industrial production.

Description

Technical field: [0001] The invention belongs to the technical field of medicine synthesis, and specifically refers to a preparation method of 5-bromouracil. Background technique: [0002] 5-Bromouracil is a synthetic base analogue. In organisms, 5-bromouracil is similar to thymine. Since the nucleic acid containing 5-bromouracil is highly sensitive to light, it can be applied to selectively destroy cells and artificial mutagenesis, and can also be used as a tracer. in the living body. 5-Bromouracil is also a drug that is used to treat inflammatory cells, among other things. As a very useful drug intermediate, 5-bromopyrimidine derivatives can be used to obtain a large number of new physiologically active drugs through coupling reactions, and are important for new small molecule targeted anti-breast cancer (such as Palbociclib, Ribociclib, Abemaciclib). intermediate. [0003] At present, the bromination method of pyrimidine derivatives is mainly in the Br 2 -H 2 O (Jou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/553
Inventor 沈永淼鲁颖颖季衡彭风梁学正陶菲菲朱露露
Owner 日照新睿招商发展有限公司
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