The Synthetic Routes of N-(2-Chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine

Synthesis of N-(2-Chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine: A Comprehensive Review

Indazoles are a class of organic compounds that have found widespread use in the pharmaceutical industry due to their diverse range of properties, including activity as HIV protease inhibitors, benzodiazepine receptor antagonists, and muscarinic antagonists.
One such indazole, N-(2-chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine, has garnered significant attention in recent years due to its potential as an antiviral agent.

There are several synthetic routes available for the synthesis of N-(2-chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine, each with its own advantages and disadvantages.
In this article, we will review the most commonly used synthetic routes, including the classic synthesis, the modified synthesis, the one-pot synthesis, the Suzuki-Miyaura synthesis, the Stille synthesis, and the Sonogashira synthesis.

Classic Synthesis

The classic synthesis of N-(2-chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine involves a multi-step process that involves the synthesis of the intermediate 2-(2-chloro-4-pyrimidinylamino)-5-methyl-benzimidazole, followed by its condensation with 2,3-dimethyl-2H-indazole-6-amine.
This method requires the use of several reagents and hazardous chemicals, and has been associated with several drawbacks, including low yield and poor purity of the final product.

Modified Synthesis

The modified synthesis of N-(2-chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine involves the use of a modified intermediate, 2-(2-chloro-4-pyrimidinylamino)-5-methyl-benzimidazole, which is prepared using a one-pot reaction.
This method offers several advantages over the classic synthesis, including higher yield and better purity of the final product.

One-Pot Synthesis

The one-pot synthesis of N-(2-chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine involves the simultaneous synthesis of the intermediate 2-(2-chloro-4-pyrimidinylamino)-5-methyl-benzimidazole and 2,3-dimethyl-2H-indazole-6-amine, using a single set of reagents.
This method offers several advantages over the classic and modified syntheses, including reduced number of steps, lower cost, and less waste generation.

Suzuki-Miyaura Synthesis

The Suzuki-Miyaura synthesis of N-(2-chloro-4-pyrimidinyl)-2,3-dimethyl-2H-indazol-6-amine involves the use of a palladium catalyst and a phosphine ligand to couple 2-chloro-4-pyrimidine with 2,3-dimethyl-2H-indazole-6-amine.
This method offers several advantages over the other synthetic routes, including high yield, ease of execution, and mild reaction conditions.

Stille Synthesis

The Stille synthesis of N-(2-chloro-4-pyrim