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The production process of methyl 5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxylate involves several steps, all of which must be carefully controlled to ensure the yield and quality of the final product.
The following is a detailed overview of the production process for this compound in the chemical industry.
- Preparation of the Starting Materials
The production of methyl 5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxylate begins with the preparation of the starting materials.
This involves the synthesis of 2-bromo-5-methylpyrimidine and 2-methylsulfonylpyrimidine, which are then combined to form the target compound. - Bromination of 2-methylpyrimidine
The first step in the synthesis of 2-bromo-5-methylpyrimidine is the bromination of 2-methylpyrimidine.
This is typically accomplished using hydrogen bromide (HBr) as the brominating agent.
The bromination reaction is typically carried out in the presence of a solvent such as ether or benzene, and is typically catalyzed by a metal salt, such as sodium hydroxide. - Protection of the N-Bromo Pyrimidine
After the bromination reaction is complete, the N-bromo pyrimidine is protected with a protecting group.
This is typically accomplished by treating the N-bromo pyrimidine with acetyl chloride to form the acetylated derivative. - Methylation of the Pyrimidine Ring
Next, the pyrimidine ring is methylated using a methylating agent, such as dimethyl sulfate (DMS).
The methylation reaction is typically carried out in the presence of a solvent, such as pyridine, and is typically catalyzed by a metal catalyst, such as zinc chloride. - Sulfonylation of the Pyrimidine Ring
After the methylation reaction is complete, the pyrimidine ring is sulfonylated using a sulfur trioxide (SO3) source, such as pyridine sulfur trioxide (PST).
The sulfonylation reaction is typically carried out in the presence of a solvent, such as pyridine, and is typically catalyzed by a metal catalyst, such as zinc chloride. - Decoloration of the Pyrimidine Ring
After the sulfonylation reaction is complete, the pyrimidine ring is decolorized using a reducing agent, such as lithium aluminum hydride (LiAlH4).
The decolorization reaction is typically carried out in the presence of a solvent, such as ether, and is typically catalyzed by a metal catalyst, such as hydrogen chloride. - Carboxylation of the Pyrimidine Ring
Finally, the pyrimidine ring is carboxylated using a carboxylating agent, such as carbon monoxide (CO) in the presence of a metal catalyst, such as iron (Fe).
The carboxylation reaction is typically carried out in the presence of a solvent, such as ethanol, and is typically heated to promote the reaction. - Purification of the Product
After the carboxylation reaction is complete, the product is purified to remove any remaining impurities.
This may involve utilizing methods such as crystallization, filtration, or chromatography.
In conclusion, the production process of methyl 5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxylate involves several steps, all of which must be carefully controlled to ensure the yield and quality