2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide
[CAS# 1211443-61-6]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide
• Molecular Formula: C₁₄H₁₇ClN₄O
• Molecular Weight: 292.76
• CAS Registry Number: 1211443-61-6
• EC Number: 808-234-2
• SMILES: CN(C)C(=O)C1=CC2=CN=C(N=C2N1C3CCCC3)Cl

Properties

• Solubility: Slightly soluble (7 g/L) (25 $degree$C), Calc.^*
• Density: 1.40$+/-$0.1 g/cm³ (20 $degree$C 760 Torr), Calc.^*
• Index of refraction: 1.678 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H317-H402-H412
• Safety Statements: P261-P264-P270-P272-P273-P280-P301+P317-P302+P352-P321-P330-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	4	H302
Acute hazardous to the aquatic environment	Aquatic Acute	3	H402

Discovery and Applications

2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide is a heterocyclic compound belonging to the pyrrolopyrimidine class, which has been extensively studied for its potential applications in medicinal chemistry. Pyrrolopyrimidines are fused bicyclic systems composed of a pyrrole ring fused to a pyrimidine, and this scaffold is widely recognized for its ability to interact with biological targets such as kinases and nucleic acid-processing enzymes. The inclusion of substituents such as a chloro group, a cyclopentyl moiety, and a dimethylated carboxamide provides both steric and electronic diversity that is useful in modulating biological activity and optimizing pharmacological properties. The discovery of pyrrolopyrimidine derivatives as bioactive molecules dates back to research on nucleoside analogs and heterocyclic scaffolds for antiviral and anticancer drug development. The pyrrolopyrimidine framework mimics structural features of purine nucleobases, which allows these compounds to interact with enzymes involved in DNA and RNA synthesis, as well as signaling kinases that regulate cell proliferation. Researchers identified that strategic substitution at positions on the pyrrolopyrimidine ring can enhance selectivity, improve solubility, and influence receptor or enzyme binding, making compounds such as 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide valuable for drug discovery studies. The synthesis of this compound generally involves construction of the fused pyrrolopyrimidine core followed by selective functionalization. The chloro substituent at the 2-position is typically introduced via halogenation reactions on the pyrimidine ring, which provides a reactive site for potential nucleophilic substitutions or cross-coupling reactions. The cyclopentyl group at the 7-position is installed to enhance lipophilicity and to provide steric bulk that can influence binding interactions within enzyme active sites. The N,N-dimethyl carboxamide at the 6-position is introduced through amide formation, which contributes hydrogen-bonding capability and further modulates physicochemical properties. Compounds of this class have been explored for their activity as kinase inhibitors. The pyrrolopyrimidine scaffold is recognized as a privileged structure in kinase drug design due to its ability to occupy the ATP-binding pocket and interact with conserved residues in the catalytic domain. Structural modifications such as the chloro substituent, cyclopentyl ring, and dimethylamide allow chemists to fine-tune potency and selectivity toward specific kinases, which is critical in the development of targeted therapies for cancer and inflammatory diseases. In addition to kinase inhibition, pyrrolopyrimidine carboxamide derivatives have been studied as potential inhibitors of other enzymatic targets, including nucleic acid polymerases and transferases. The electronic and steric properties imparted by the chloro, cyclopentyl, and dimethylamide groups help optimize binding affinity and pharmacokinetic characteristics, including metabolic stability and solubility. These features make the compound a versatile intermediate for further derivatization in medicinal chemistry programs. Beyond biological applications, the compound serves as a model system for exploring structure-activity relationships in heterocyclic chemistry. By systematically varying substituents on the pyrrolopyrimidine core, researchers can study how steric hindrance, electronic effects, and hydrogen-bonding interactions influence binding and reactivity. Such studies provide valuable insights that guide the design of new bioactive molecules with improved efficacy and selectivity. Overall, 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide exemplifies a strategically substituted pyrrolopyrimidine derivative. Its fused heterocyclic structure, combined with targeted substitutions, enables applications in kinase inhibition, enzyme modulation, and medicinal chemistry research. The compound illustrates how rational design of heterocyclic scaffolds can provide versatile chemical frameworks for drug discovery and synthetic methodology development.

References

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