The Synthetic Routes of 2-(METHYLTHIO)[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-7-AMINE

The synthesis of 2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine is an important goal in the pharmaceutical industry due to its potential as an anti-cancer and anti-inflammatory drug.
There are several synthetic routes to this compound, each with its own advantages and disadvantages.

One of the most common synthetic routes to 2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine is the Stille reaction.
This method involves the reaction of 2-chloro-6-methylbenzothiazole with 2-aminopyrimidine-7-boronic acid.
The resulting product is then reduced with lithium aluminum hydride to form the desired amine.
This route has the advantage of using easily available starting materials and is relatively straightforward.
However, it also has some disadvantages, such as the need for handling hazardous reagents and the potential for impurity formation.

Another synthetic route to 2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine involves the use of a Pd/C catalyst for the coupling of 2-iodothiophene-7-boronic acid with 2-amino-5-chloropyrimidine.
This method has the advantage of using a catalyst that is easily prepared and can be recycled, making it more environmentally friendly.
However, the starting materials used in this route are more expensive and harder to obtain than those used in the Stille reaction.

A third synthetic route involves the use of a palladium catalyst for the coupling of 2-chlorothiophene-7-boronic acid with β-amino-β-methyl amide.
The resulting product is then hydrogenated to remove the boronic acid group and form the desired amine.
This route has the advantage of using a simple and inexpensive starting material, but requires a more complex reaction sequence and the use of a more expensive catalyst.

Overall, the selection of a synthetic route to 2-(methylthio)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine will depend on the availability and cost of the starting materials, the desired yield and purity of the product, and the availability of suitable catalysts and reaction conditions.