Tert-butyl 4-(5-(4-fluorobenzoyl)pyrimidin-2-yl)piperazine-1-carboxylate
[CAS# 1703794-73-3]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Tert-butyl 4-(5-(4-fluorobenzoyl)pyrimidin-2-yl)piperazine-1-carboxylate
• Molecular Formula: C₂₀H₂₃FN₄O₃
• Molecular Weight: 386.42
• CAS Registry Number: 1703794-73-3
• SMILES: CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=C(C=N2)C(=O)C3=CC=C(C=C3)F

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 544.6±60.0 ºC 760 mmHg (Calc.)^*
• Flash point: 283.2±32.9 ºC (Calc.)^*
• Index of refraction: 1.567 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+351+338-P302+352

Discovory and Applicatios

Tert-butyl 4-(5-(4-fluorobenzoyl)pyrimidin-2-yl)piperazine-1-carboxylate is a complex organic compound that features several key structural components: a piperazine ring, a pyrimidine core, a fluorobenzoyl group, and a tert-butyl ester group. The piperazine ring serves as a six-membered heterocycle, which is commonly found in pharmacologically active compounds due to its ability to interact with biological targets, particularly in the central nervous system. The pyrimidine ring, containing nitrogen atoms at the 1 and 3 positions, is also crucial for biological activity, often involved in the binding to specific receptors or enzymes.

This compound consists of a fluorobenzoyl group attached at the 5-position of the pyrimidine ring. The fluorine atom, placed at the para position of the benzoyl group, introduces electron-withdrawing characteristics that can influence the compound’s lipophilicity and its interactions with biological targets. The tert-butyl ester group at the 1-position of the piperazine ring serves as a protective group, enhancing the molecule's stability and potentially modulating its bioavailability or pharmacokinetic properties.

Synthesis of this compound typically involves multiple steps, starting with the preparation of the pyrimidine derivative, which can be achieved through a variety of synthetic methods including nucleophilic substitution or cyclization reactions. The introduction of the fluorobenzoyl group is often carried out through electrophilic aromatic substitution, where the pyrimidine derivative is reacted with 4-fluorobenzoyl chloride in the presence of a base such as pyridine or triethylamine. The final step of the synthesis involves esterification of the piperazine amine with a suitable tert-butyl ester reagent, such as tert-butyl chloroformate or tert-butyl alcohol in the presence of a coupling agent like DCC (dicyclohexylcarbodiimide).

The compound holds potential in medicinal chemistry, where it can be explored for its activity as a ligand for biological receptors or enzymes, particularly those involved in the central nervous system or in the regulation of cellular pathways. The pyrimidine ring, often involved in the inhibition of kinases or other enzyme classes, could provide valuable interactions with biological targets, while the piperazine ring can confer receptor selectivity or act as a pharmacophore for drug development.

The fluorobenzoyl group adds rigidity and electronic influence to the molecule, which may enhance interactions with hydrophobic pockets of protein targets. Additionally, the tert-butyl ester group provides both steric protection and modulation of the molecule’s overall size, which is a useful property for fine-tuning drug-like properties such as permeability or metabolic stability.

In the context of drug discovery, compounds similar to tert-butyl 4-(5-(4-fluorobenzoyl)pyrimidin-2-yl)piperazine-1-carboxylate are often explored for their potential as part of fragment-based screening libraries, where the goal is to identify small, bioactive molecules that can be further optimized into potent and selective therapeutics. The combination of heterocycles, fluorine substitution, and ester functionalities makes this molecule a useful building block for drug development, particularly in the search for new classes of pharmaceutical agents targeting specific receptors or enzymes involved in disease pathways.