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2-(Methylthio)-alpha-oxo-4-pyrimidineacetic acid ethyl ester is a synthetic compound that is widely used in the chemical industry.
It is a key intermediate in the synthesis of several important chemicals, including pharmaceuticals, agrochemicals, and dyes.
In this article, we will discuss the synthetic routes of 2-(Methylthio)-alpha-oxo-4-pyrimidineacetic acid ethyl ester and the applications of this compound in the chemical industry.
Synthetic routes of 2-(Methylthio)-alpha-oxo-4-pyrimidineacetic acid ethyl ester
There are several synthetic routes for the preparation of 2-(Methylthio)-alpha-oxo-4-pyrimidineacetic acid ethyl ester.
The most common methods include the following:
- via a Halogenation: This involves the treatment of 2-(dimethylamino)-4-oxo-4H-pyrimidin-3-thiol with a halogenating agent such as chlorine or bromine in the presence of a solvent such as acetone, dichloromethane or chloroform.
The resulting product is then treated with an ethylating agent such as ethyl iodide in the presence of a catalyst such as sodium hydroxide.
This method is relatively simple and provides a good yield of the desired product. - via a Reductive Amination: This involves the treatment of 2-(dimethylamino)-4-oxo-4H-pyrimidin-3-thiol with an aldehyde such as acetaldehyde in the presence of a reducing agent such as lithium aluminum hydride (LiAlH4) in a solvent such as N,N-dimethylformamide (DMF).
The resulting product is then treated with an ethylating agent such as ethyl iodide in the presence of a catalyst such as sodium hydroxide.
This method is also relatively simple and provides a good yield of the desired product. - via a Reductive Halogenation: This involves the treatment of 2-(dimethylamino)-4-oxo-4H-pyrimidin-3-thiol with a halogenating agent such as chlorine or bromine in the presence of a reducing agent such as triphenylphosphine (PPh3) in a solvent such as dichloromethane or chloroform.
The resulting product is then treated with an ethylating agent such as ethyl iodide in the presence of a catalyst such as sodium hydroxide.
This method provides a good yield of the desired product, but requires careful control of the reaction conditions to avoid unwanted side reactions.
Applications of 2-(Methylthio)-alpha-oxo-4-pyrimidineacetic acid ethyl ester
2-(Methylthio)-alpha-oxo-4-pyrimidineacetic acid ethyl ester is a versatile intermediate that is used in the synthesis of a wide range of chemicals, including pharmaceuticals, agrochemicals, and dyes.
Some of the most important applications of this compound include:
- Pharmaceuticals: 2-(Methylthio)-alpha-oxo-4-pyrimidineacetic acid ethyl ester is used in the synthesis of several important pharmaceuticals, including antibiotics, anti-inflammatory drugs, and chemotherapy agents.
For example, it is a key intermediate in the synthesis of the antibiotic erythromycin and the anti-inflammatory drug naproxen. - Agrochemicals: 2-(Methylthio)-alpha-oxo-4-pyrimid