The Synthetic Routes of 3-(2-Methyl-4-pyrimidinyl)benzenamine

3-(2-Methyl-4-pyrimidinyl)benzenamine is a compound that has found wide applications in the chemical industry due to its unique properties and versatile chemical reactivity.
This compound is commonly used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other chemical products.
In this article, we will discuss some of the synthetic routes to 3-(2-Methyl-4-pyrimidinyl)benzeneamine.

1. Mannich reaction
   One of the most widely used methods for the synthesis of 3-(2-Methyl-4-pyrimidinyl)benzenamine is the Mannich reaction.
   In this reaction, a primary or secondary amine is reacted with formaldehyde and a substituted phenol in the presence of an aqueous alkaline solution.
   The reaction proceeds through a series of steps, including the formation of an imine intermediate, which is then hydrolyzed to give the desired amine.
   
2. Electrophilic substitution
   3-(2-Methyl-4-pyrimidinyl)benzenamine can also be synthesized by electrophilic substitution reactions, such as halogenation, nitration, and sulfonation.
   For example, chlorination of 3-bromo-2-methyl-4-pyrimidine with hydrogen chloride in the presence of a Lewis acid yields the desired amine.
   Similarly, nitration of 3-(2-methyl-4-pyrimidinyl)benzene with nitrating sulfuric acid gives 3-(2-methyl-4-pyrimidinyl)benzenamine.
   
3. Reductive nitration
   Another route to 3-(2-Methyl-4-pyrimidinyl)benzenamine is reductive nitration, which involves the reduction of a nitro compound to an amine.
   In this reaction, a nitro compound is reduced with a reducing agent, such as lithium aluminum hydride, in the presence of a solvent, such as ether or THF.
   The reduction of a nitro compound to an amine can be carried out using other reducing agents, such as sodium borohydride or hydrogenation over a catalyst.
   
4. Direct amination
   3-(2-Methyl-4-pyrimidinyl)benzenamine can also be synthesized by direct amination of 3-bromo-2-methyl-4-pyrimidine with an amine, such as NH2OH or NH3.
   This reaction can be carried out in the presence of a solvent, such as DMF or DME, and a metal catalyst, such as palladium or rhodium.
   
5. Hydrolysis of ester
   Another synthetic route to 3-(2-Methyl-4-pyrimidinyl)benzenamine is the hydrolysis of an ester, such as the corresponding pyrimidine-2,4-dione.
   This reaction can be carried out in the presence of a solvent, such as water, and a base, such as sodium hydroxide.
   

In conclusion, 3-(2-Methyl-4-pyrimidinyl)benzenamine can be synthesized by a variety of methods, including the Mannich reaction, electrophilic substitution, reductive nitration, direct amination, and hydrolysis of ester.
The choice of synthetic route depends on factors such as the availability of reagents, the desired yield, and the cost of the reaction.