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Synthetic method of 2'-Deoxy-2'-fluorouridine

A synthesis method and technology of deoxyuridine, applied in chemical instruments and methods, sugar derivatives, organic chemistry and other directions, can solve the problems of high equipment requirements, high degree of risk, unsuitable for scale-up production, etc., and achieve high reaction conversion rate, good yield

Active Publication Date: 2021-03-16
平江县吉成科技有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] 2'-Fluoro-2'-deoxyuridine is an important pharmaceutical and chemical intermediate. It is generally synthesized by uridine. Firstly, the 2'-position and 1-position keto group are dehydrated and condensed, and then fluorinated reagents are used in the 2 The '-position introduces a fluorine group, and US2004 / 77567 A1 reported that the 2'-position of uridine and the 1-position ketone group were dehydrated and condensed, and then reacted in 70% hydrogen fluoride in pyridine solution to synthesize 2'-fluoro-2'-deoxyuridine , the reaction requires high equipment and high risk, and will produce a large amount of fluorine-containing acidic wastewater, which is not suitable for large-scale production

Method used

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  • Synthetic method of 2'-Deoxy-2'-fluorouridine
  • Synthetic method of 2'-Deoxy-2'-fluorouridine

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Experimental program
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Effect test

Embodiment 1

[0020] The synthesis of embodiment 1 compound 2

[0021] Add 69.0g uridine to the reaction flask, add 69.0g (1.1eq) diphenyl carbonate, add 163.0g DMF, start stirring, and gradually raise the temperature to 58-62°C. During the heating process, the solid dissolves continuously. At about 60°C, Solution clarification After the solution is clarified, control the temperature at 58-62°C, then add 1.7g of sodium bicarbonate and gradually raise the temperature to 78-82°C. After the reaction is completed, naturally cool down to 20°C-30°C, stir for 1-3 hours, and filter. The filter cake was dried to obtain 57.2g of compound 2, yield: 89.5%, purity: 99.57%.

Embodiment 2

[0022] The synthesis of embodiment 2 compound 3

[0023] Add 20g of compound 2 to the reaction flask, add 12.5g of highly active anhydrous potassium fluoride, 0.2g of boron trifluoride ether, 200ml of DMF, heat up to 120°C for 12 hours, filter after the reaction is completed, concentrate the filtrate, and use tetrahydrofuran and ethyl acetate The ester was recrystallized to obtain 11.6 g of 2'-fluoro-2'-deoxyuridine, with a yield of 53.2% and a purity of 98.2%.

Embodiment 3

[0024] The synthesis of embodiment 3 compound 3

[0025] Add 20g of compound 2 to the reaction flask, add 12.5g of highly active anhydrous potassium fluoride, 0.2g of boron trifluoride ether, and 200ml of chlorobenzene, heat up to 130°C for 12 hours, filter after the reaction is completed, concentrate the filtrate, and use tetrahydrofuran and Recrystallized from ethyl acetate to obtain 10.8 g of 2'-fluoro-2'-deoxyuridine with a yield of 49.8% and a purity of 99.0%.

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Abstract

The application discloses a synthetic method of 2'-deoxy-2'-fluorouridine. The synthetic method comprises the following steps: step 1) adding uridine and diphenyl carbonate into dimethylformamide, performing heating for dissolving, after a solution is clear, adding a catalyst namely sodium bicarbonate under the condition of keeping the temperature, performing heating for the second time for a reaction, performing natural cooling to room temperature after the reaction is finished, performing stirring, performing filtering, and drying a filter cake to obtain a compound 2; and step 2) dissolvingthe compound 2, anhydrous potassium fluoride and a catalyst namely boron trifluoride diethyl etherates in a solvent, performing a heating reaction, and performing filtration and concentration after the reaction is completed to obtain a compound 3, namely the 2'-Deoxy-2'-fluorouridine. The method provided by the invention has the advantages of higher reaction conversion rate and better yield, and avoids the use of hydrogen fluoride pyridine, fluorine gas and other high-toxicity reagents.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a synthesis method of 2'-fluoro-2'-deoxyuridine. Background technique [0002] 2'-Fluoro-2'-deoxyuridine is an important pharmaceutical and chemical intermediate. It is generally synthesized by uridine. Firstly, the 2'-position and 1-position keto group are dehydrated and condensed, and then fluorinated reagents are used in the 2 The '-position introduces a fluorine group, and US2004 / 77567 A1 reported that the 2'-position of uridine and the 1-position ketone group were dehydrated and condensed, and then reacted in 70% hydrogen fluoride in pyridine solution to synthesize 2'-fluoro-2'-deoxyuridine , the reaction requires high equipment and high risk, and will produce a large amount of fluorine-containing acidic wastewater, which is not suitable for scale-up production. Contents of the invention [0003] The main purpose of this application is to provide a kind of syn...

Claims

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Application Information

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IPC IPC(8): C07H19/073C07H1/00
CPCC07H19/073C07H1/00
Inventor 刘助武廖福爱
Owner 平江县吉成科技有限责任公司
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