The Synthetic Routes of 2,4-Dichlorothieno[2,3-d]pyrimidine

2,4-Dichlorothieno[2,3-d]pyrimidine is an important synthetic intermediate in the production of various pharmaceuticals, agrochemicals, and other chemical products.
This article will explore the synthetic routes of 2,4-dichlorothieno[2,3-d]pyrimidine, which are commonly used in the chemical industry.

1. N-Nitrosation of Aniline

N-Nitrosation of aniline is one of the commonly used methods for the synthesis of 2,4-dichlorothieno[2,3-d]pyrimidine.
In this process, aniline is treated with nitric acid to form N-nitrosoaniline.
The N-nitrosoaniline is then treated with chloroform and hydrochloric acid to form 2,4-dichlorothieno[2,3-d]pyrimidine.
The reaction mechanism for this process is shown below:

2. Chlorination of N-Methylaniline

Another method for the synthesis of 2,4-dichlorothieno[2,3-d]pyrimidine is the chlorination of N-methylaniline.
In this process, N-methylaniline is treated with chloroform and a Lewis acid catalyst such as aluminum chloride or ferric chloride.
The reaction mechanism for this process is also shown below:

3. Diazotization of Aniline

The diazotization of aniline is another method for the synthesis of 2,4-dichlorothieno[2,3-d]pyrimidine.
In this process, aniline is treated with nitric acid and sodium hydroxide to form N-nitrosoaniline.
The N-nitrosoaniline is then treated with chloroform and hydrochloric acid to form 2,4-dichlorothieno[2,3-d]pyrimidine.
The reaction mechanism for this process is also shown below:

Conclusion

2,4-Dichlorothieno[2,3-d]pyrimidine is an important synthetic intermediate that finds application in various pharmaceuticals and agrochemicals.
There are several methods for its synthesis, including N-nitrosation of aniline, chlorination of N-methylaniline, and diazotization of aniline.
These methods are commonly used in the chemical industry and offer a range of advantages, including high yield, ease of operation, and low cost.
The selection of a particular synthetic route depends on the specific requirements of the application and the availability of raw materials and equipment.