4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine
[CAS# 941685-27-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine
• Synonyms: 4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole
• Molecular Formula: C₁₅H₂₁N₅OSi
• Molecular Weight: 315.45
• CAS Registry Number: 941685-27-4
• EC Number: 801-232-2
• SMILES: C[Si](C)(C)CCOCN1C=CC2=C(N=CN=C21)C3=CNN=C3

Properties

• Solubility: Insoluble (1.0E^-3 g/L) (25 °C), Calc.^*
• Density: 1.20±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.607, Calc.^*
• Boiling Point: 501.8±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 257.3±30.1 °C, Calc.^*

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

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine is a complex organic compound that belongs to the class of pyrrolo[2,3-d]pyrimidine derivatives. This compound consists of several functional groups, including a pyrazole ring, a pyrrolo[2,3-d]pyrimidine structure, and a trimethylsilyl group. These structural features contribute to its unique chemical properties, which have been explored in the context of drug development and chemical synthesis.

The synthesis of 4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine is typically achieved through various organic reactions that involve the construction of the pyrimidine core, pyrazole ring, and the introduction of the trimethylsilyl group. These methods ensure that the compound is synthesized in a controlled and efficient manner, making it accessible for use in various chemical applications.

This compound has gained attention for its potential application in medicinal chemistry. The pyrrolo[2,3-d]pyrimidine structure is known to possess bioactivity, particularly in the development of small molecule inhibitors that can target specific enzymes and proteins. The presence of the pyrazole group and the trimethylsilyl ether can influence the compound’s ability to interact with biological targets, enhancing its potential as a therapeutic agent. Although specific applications in drug development are still under investigation, pyrrolo[2,3-d]pyrimidine derivatives have been shown to exhibit properties that could be useful in treating a variety of diseases, particularly cancers and neurodegenerative disorders.

Additionally, the trimethylsilyl group in the structure plays a critical role in improving the compound’s solubility and stability, which are essential factors for its bioavailability and efficacy in pharmaceutical formulations. This functional group also contributes to the compound’s ability to cross biological membranes, which is a crucial characteristic for drugs designed to act within living organisms.

The use of 4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine in material science is another potential application. Its structural features, particularly the ability of the pyrazole and pyrimidine rings to interact with different materials, open up possibilities for the development of new functional materials, such as molecular sensors or catalysts.

Overall, 4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine is a promising compound with potential applications in medicinal chemistry, material science, and other areas. Its structural characteristics and bioactivity make it a subject of ongoing research, with its applications likely to expand as further studies are conducted. The compound’s functional groups contribute to its versatility, making it a valuable candidate for drug development and other industrial applications.

References

2024. A comprehensive review on synthetic strategy and MOA of marketed drugs having therapeutically potential chemical entity pyrazole. Journal of the Iranian Chemical Society.
DOI: 10.1007/s13738-024-03095-7