Methyl imidazo[1,2-a]pyrimidine-5-carboxylate
[CAS 2120540-87-4]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl imidazo[1,2-a]pyrimidine-5-carboxylate
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.16
• CAS Registry Number: 2120540-87-4
• SMILES: COC(=O)C1=CC=NC2=NC=CN12

Properties

• Density: 1.4$+/-$0.1 g/cm³ Calc.^*
• Index of refraction: 1.649 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Methyl imidazo[1,2-a]pyrimidine-5-carboxylate is a fused heterocyclic compound containing an imidazo–pyrimidine ring system bearing a methyl ester functional group at the 5-position. Compounds of the imidazo[1,2-a]pyrimidine family belong to a broader class of nitrogen-rich fused heterocycles that have been extensively studied in organic and medicinal chemistry due to their structural rigidity, electron-deficient aromatic systems, and versatility as synthetic intermediates.

The development of imidazo-fused heterocycles is closely associated with advances in heterocyclic chemistry during the twentieth century, when synthetic methods for constructing fused nitrogen-containing rings became increasingly efficient. The imidazo[1,2-a]pyrimidine scaffold was of particular interest because it combines two electron-deficient heterocycles, resulting in a conjugated system with distinct electronic properties compared with monocyclic pyrimidines or imidazoles. This structural motif has been explored in both fundamental chemical studies and applied research.

Methyl imidazo[1,2-a]pyrimidine-5-carboxylate contains a carboxylate ester group at the 5-position of the fused ring system. The presence of this ester functionality provides a reactive site for further chemical transformations. Esters of heterocyclic carboxylic acids are commonly used in organic synthesis because they can be converted into a wide range of derivatives, including amides, acids, and other functionalized compounds. This makes the compound a useful intermediate in synthetic chemistry.

The fused imidazo[1,2-a]pyrimidine core is typically constructed through cyclization reactions involving appropriately substituted aminopyrimidines and carbonyl-containing reagents. Such synthetic strategies have been widely employed in heterocyclic chemistry to access structurally diverse fused ring systems. Once formed, the resulting scaffold can be functionalized at various positions, including carboxylation or esterification at the 5-position, leading to derivatives such as methyl imidazo[1,2-a]pyrimidine-5-carboxylate.

Compounds containing the imidazo[1,2-a]pyrimidine framework have been investigated in medicinal chemistry due to their potential biological activity. The rigid bicyclic structure and multiple nitrogen atoms allow for hydrogen bonding interactions and binding to biological macromolecules. As a result, derivatives of this scaffold have been studied in research programs targeting enzymes and receptors, although specific biological activity depends strongly on substitution patterns.

The ester group in methyl imidazo[1,2-a]pyrimidine-5-carboxylate also plays an important role in modulating physicochemical properties. Esterification generally increases lipophilicity compared with the corresponding carboxylic acid, which can influence solubility, permeability, and reactivity. In synthetic sequences, the methyl ester can serve as a protected form of the carboxylic acid, allowing selective reactions elsewhere on the molecule before hydrolysis is performed to regenerate the acid functionality.

From a materials chemistry perspective, fused heterocycles such as imidazo[1,2-a]pyrimidines have been explored for their electronic properties, including potential applications in fluorescent materials and organic electronic systems. The conjugated nitrogen-rich ring system can influence الضوء absorption and emission characteristics, although such applications depend strongly on substitution patterns and extended conjugation.

Analytical characterization of compounds like methyl imidazo[1,2-a]pyrimidine-5-carboxylate is typically carried out using standard spectroscopic methods, including nuclear magnetic resonance spectroscopy and mass spectrometry. These techniques allow confirmation of ring fusion, substitution pattern, and functional group identity, which are critical for verifying synthetic products in heterocyclic chemistry.

Overall, methyl imidazo[1,2-a]pyrimidine-5-carboxylate is a fused nitrogen heterocycle featuring an ester functional group that serves as a versatile intermediate in organic synthesis. Its importance lies in its role as a building block for further chemical modification, its presence within a structurally significant heterocyclic scaffold, and its relevance to broader studies in heterocyclic and medicinal chemistry.