The Synthetic Routes of 4,6-Dichloro-2-methanesulfinyl-pyrimidine

4,6-Dichloro-2-methanesulfinyl-pyrimidine is an important intermediate in the production of various pharmaceuticals, agrochemicals, and other chemical products.
It is also known as 4,6-dichloro-2-methanesulfonylpyrimidine or DACA.
The compound is synthesized through various routes in the chemical industry, and this article will discuss some of the most commonly used synthetic routes.

Route 1: Via 4-Chloro-6-methylpyrimidine-2,4(1H,3H)-dione

One of the most popular routes to synthesize 4,6-dichloro-2-methanesulfinyl-pyrimidine involves the synthesis of 4-chloro-6-methylpyrimidine-2,4(1H,3H)-dione as an intermediate.
This compound can be prepared by reacting 4-chloro-6-methylpyrimidine with 2,4-dinitrophenylhydrazine in the presence of a base such as sodium hydroxide or potassium hydroxide.
The resulting 4-chloro-6-methylpyrimidine-2,4(1H,3H)-dione can then be treated with hydrochloric acid to produce 4,6-dichloro-2-methanesulfinyl-pyrimidine.

Route 2: Via 4-Chloro-6-chloromethylpyrimidine

Another common route to synthesize 4,6-dichloro-2-methanesulfinyl-pyrimidine involves the synthesis of 4-chloro-6-chloromethylpyrimidine as an intermediate.
This compound can be prepared by reacting 4-chloro-6-methylpyrimidine with chloromethylzinc in the presence of a polar solvent such as DMF.
The resulting 4-chloro-6-chloromethylpyrimidine can then be treated with hydrazine to produce 4,6-dichloro-2-methanesulfinyl-pyrimidine.

Route 3: Via 4-Chloro-6-methylpyrimidin-2-one

A third route to synthesize 4,6-dichloro-2-methanesulfinyl-pyrimidine involves the synthesis of 4-chloro-6-methylpyrimidin-2-one as an intermediate.
This compound can be prepared by reacting 4-chloro-6-methylpyrimidine with cyclohexanone in the presence of a Lewis acid catalyst such as aluminum chloride or sulfuric acid.
The resulting 4-chloro-6-methylpyrimidin-2-one can then be treated with sodium hydride and a polar solvent such as DMF to produce 4,6-dichloro-2-methanesulfinyl-pyrimidine.

Route 4: Via N-Chlorosuccinimide

A fourth route to synthesize 4,6-dichloro-2-methanesulfinyl-pyrimidine involves the synthesis of N-chlorosuccinimide as an intermediate.
This compound can be prepared by reacting nitrosylsulfonate with succinimide in the presence of a solvent such as acetonitrile.
The resulting N-chlorosuccinimide can then be treated with 4-chloro-6-methylpyrimidine and a Lewis acid catalyst such as zinc chloride to produce 4,