The Production Process of Pyrimidine, 4-(trifluoromethyl)- (9CI)

The production process of pyrimidine, 4-(trifluoromethyl)- (9CI), is a complex and multi-step process that involves several chemical reactions and purification steps.
The following is an overview of the production process of 4-(trifluoromethyl)-pyrimidine (9CI) in the chemical industry.

Step 1: Synthesis of 4-Trifluoromethyl-2,5-diaminotoluene (2)
The first step in the production of 9CI is the synthesis of 4-trifluoromethyl-2,5-diaminotoluene (2).
This compound is synthesized by reacting 2,5-dimethoxytoluene (1) with hexafluorobenzene in the presence of a strong acid catalyst such as sulfuric acid.
The reaction produces 4-trifluoromethyl-2,5-diaminotoluene (2) and the corresponding salt.

Step 2: Condensation of 4-Trifluoromethyl-2,5-diaminotoluene (2)
The next step is the condensation of 4-trifluoromethyl-2,5-diaminotoluene (2) with another molecule of 2,5-diaminotoluene (2), in the presence of a condensation agent such as dicyclohexylcarbodiimide (DCC) and hydroxyquinoline (HQ).
This reaction forms a new compound, 4-(trifluoromethyl)-1,3-oxazolidin-2-one (3).

Step 3: Reduction of 4-(Trifluoromethyl)-1,3-oxazolidin-2-one (3)
The next step is the reduction of 4-(trifluoromethyl)-1,3-oxazolidin-2-one (3) to form 4-(trifluoromethyl)-pyrimidine-2,5-dione (4).
This reduction is usually carried out using a reducing agent such as lithium aluminum hydride (LiAlH4) in the presence of a solvent such as tetrahydrofuran (THF).

Step 4: Purification of 4-(Trifluoromethyl)-pyrimidine-2,5-dione (4)
After the reduction reaction, the product 4-(trifluoromethyl)-pyrimidine-2,5-dione (4) is typically purified by crystallization or column chromotography.
This step removes any impurities that may have been present during the previous steps, resulting in a pure sample of 4-(trifluoromethyl)-pyrimidine-2,5-dione (4).

Overall, the production process of 4-(trifluoromethyl)-pyrimidine (9CI) involves several steps, including the synthesis of 4-trifluoromethyl-2,5-diaminotoluene (2), the condensation of 4-trifluoromethyl-2,5-diaminotoluene (2) with another molecule of 2,5-diaminotoluene (2), the reduction of 4-(trifluoromethyl)-1,3-oxazolidin-2-one (3) to form 4-(trifluoromethyl)-pyrimidine-2,5-dione (4), and the purification of the final product.
This process requires specialized equipment and chemical handling, and is typically carried out in a controlled environment to ensure the safety of the personnel involved and to minimize the potential for environmental contamination.