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The production process of (5-fluoro-pyrimidin-2-yl)-acetic acid, also known as 5-FU or 5-fluorouracil, is a complex and multi-step process that requires a combination of chemical reactions and purification steps.
The final product is a key intermediate in the production of a number of important drugs, including the cancer treatment drug, 5-Fluorouracil.
The Production Process:
- Preparation of precursors:
The production of (5-fluoro-pyrimidin-2-yl)-acetic acid starts with the preparation of precursors, such as 2,6-dimethyl-5-fluoro-pyrimidine and 4-[(5-fluoro-2-oxo-1,2,4-oxadiazolidin-3-yl)amino]-5-fluoropyrimidine.
These precursors are produced through a series of chemical reactions involving the reaction of 2,6-dimethyl-5-fluoro-pyrimidine with 4-aminomethyl-5-fluoro-2-oxo-1,2,4-oxadiazolidine in the presence of a catalyst. - Condensation reactions:
The next step in the production process is the condensation of the precursors.
This involves the reaction of the 4-[(5-fluoro-2-oxo-1,2,4-oxadiazolidin-3-yl)amino]-5-fluoropyrimidine precursor with other precursors in the presence of a condensation catalyst, such as HATU (O-(7-azabenzotriazole-1yl)-N,N,N',N'-tetramethyluronium iodide).
The condensation reactions lead to the formation of a series of intermediate compounds. - Purification:
The intermediate compounds produced in the condensation reactions are very unstable and require further purification to ensure the production of a pure and stable final product.
This involves the use of a variety of chromatography methods, including high-performance liquid chromatography (HPLC) and flash chromatography. - Hydrolysis:
The final step in the production process is the hydrolysis of the intermediate compound to produce the final product, (5-fluoro-pyrimidin-2-yl)-acetic acid.
This involves the treatment of the intermediate compound with water and a strong acid catalyst, such as hydrochloric acid, to cleave the protecting group and release the final product.
Challenges and Considerations:
The production process of (5-fluoro-pyrimidin-2-yl)-acetic acid is complex and requires the use of specialized equipment and chemical reagents.
The process also requires strict control over reaction conditions, such as temperature, pressure, and the use of solvents, to ensure the production of a pure final product.
One of the major challenges in the production of (5-fluoro-pyrimidin-2-yl)-acetic acid is the purification of the intermediate compounds.
This requires the use of specialized chromatography methods, such as HPLC and flash chromatography, which can be time-consuming and expensive.
In addition, the use of strong acid catalysts, such as hydrochloric acid, can pose a risk to the workers involved in the production process.
Another challenge in the production of (5-fluoro-pyrimidin-2-yl)-acetic acid is the stability of the intermediate compounds.
These compounds are very unstable and can undergo unwanted reactions if not stored and handled properly.
This requires strict control over the storage and handling of the intermediate compounds to ensure their stability and prevent contamination.
Conclusion:
The production process of (5-fluoro-pyrimidin-