(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate
[CAS# 1146629-75-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate
• Molecular Formula: C₁₂H₁₄ClN₃O₂
• Molecular Weight: 267.71
• CAS Registry Number: 1146629-75-5
• SMILES: CC(C)(C)C(=O)OCN1C=CC2=C1N=CN=C2Cl

Properties

• Solubility: Practically insoluble (0.056 g/L) (25 ºC), Calc.^*
• Density: 1.30±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate is a synthetic organic compound that has attracted attention for its potential applications in drug development, particularly in the field of cancer therapeutics. This compound features a pyrrolopyrimidine core, which is a key structural motif in many biologically active molecules. The presence of a chloro substituent at the 4-position and a pivalate ester group attached to the pyrimidine ring further enhances its chemical properties, making it a valuable intermediate in the synthesis of pharmaceutical agents.

The discovery of (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate was driven by the need to develop novel kinase inhibitors, a class of drugs that target specific enzymes involved in cell signaling pathways. Kinase inhibitors are crucial in the treatment of various cancers, as they can block the activity of proteins that promote uncontrolled cell growth. The pyrrolopyrimidine scaffold is particularly effective in this regard due to its ability to mimic the purine bases of ATP, the natural substrate of many kinases. The addition of a chloro group at the 4-position of the pyrrolopyrimidine ring enhances the compound's ability to bind selectively to the active site of kinases, thereby increasing its potency as an inhibitor.

In addition to its role in kinase inhibition, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate has also been explored as a precursor in the synthesis of other bioactive molecules. The pivalate ester group serves as a protecting group for the hydroxyl function, allowing for selective deprotection under mild conditions. This feature is particularly useful in multi-step synthetic routes where the preservation of functional groups is essential. By utilizing (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate as a building block, researchers can efficiently construct complex molecules with enhanced biological activity.

The application of (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate extends beyond oncology. It has shown potential in the development of antiviral agents, particularly those targeting viral kinases and polymerases. The compound's ability to interfere with the replication machinery of viruses makes it a promising candidate for further investigation in antiviral drug development. Additionally, its structural similarity to nucleosides suggests that it could be incorporated into nucleic acids, leading to the design of novel antiviral agents with unique mechanisms of action.

In materials science, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate has been utilized in the synthesis of functionalized polymers and other advanced materials. The compound's reactivity allows for its incorporation into polymer chains, imparting specific electronic and mechanical properties to the resulting materials. These materials have potential applications in the fields of electronics, coatings, and nanotechnology.

The discovery and subsequent application of (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate represent significant advancements in both medicinal chemistry and materials science. Its unique structure and reactivity have made it a valuable tool for researchers seeking to develop new therapeutic agents and innovative materials. As research in this area continues, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate is likely to play a pivotal role in the development of next-generation drugs and materials.