Production Method 1

19808-30-1

Reaction Conditions

Reference

Preparation of 4-substituted 5-polycyclylpyrimidine herbicides.

, World Intellectual Property Organization, , ,

Production Method 2

19808-30-1

Reaction Conditions

Reference

Chemistry of pyrimidine. II. Synthesis of pyrimidine N-oxides and 4-pyrimidinones by reaction of 5-substituted pyrimidines with peracids. Evidence for covalent hydrates as reaction intermediates

Kress, Thomas J., Journal of Organic Chemistry, 1985, 50(17), 3073-6

5-bromo-3,4-dihydropyrimidin-4-one Preparation Products

• 5-bromo-3,4-dihydropyrimidin-4-one (19808-30-1)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Halopyrimidines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives Halopyrimidines

5-Bromo-3,4-Dihydropyrimidin-4-One: A Comprehensive Overview

5-Bromo-3,4-dihydropyrimidin-4-one (CAS No. 19808-30-1) is a versatile organic compound that has garnered significant attention in the fields of organic synthesis and medicinal chemistry. This compound belongs to the class of pyrimidine derivatives, which are known for their wide-ranging applications in drug discovery and chemical synthesis. The structure of 5-bromo-3,4-dihydropyrimidin-4-one consists of a pyrimidine ring with a bromine substituent at the 5-position and a ketone group at the 4-position, making it a valuable intermediate in the construction of complex molecules.

The synthesis of 5-bromo-3,4-dihydropyrimidin-4-one typically involves multi-step reactions, often starting from readily available starting materials such as urea or thiourea. Recent advancements in catalytic methods have enabled more efficient and selective syntheses, reducing production costs and minimizing environmental impact. For instance, researchers have explored the use of microwave-assisted synthesis to accelerate reaction times while maintaining high yields. These developments highlight the compound's importance in modern chemical manufacturing.

One of the most promising applications of 5-bromo-3,4-dihydropyrimidin-4-one lies in its role as an intermediate in the synthesis of bioactive compounds. Its bromine substituent serves as an excellent leaving group, facilitating nucleophilic substitutions that can lead to diverse functionalized products. For example, recent studies have demonstrated its utility in the construction of heterocyclic frameworks with potential anticancer properties. By incorporating this compound into larger molecular structures, scientists can explore its ability to modulate cellular pathways associated with tumor growth and metastasis.

In addition to its role in drug discovery, 5-bromo-3,4-dihydropyrimidin-4-one has found applications in materials science. Its ability to form stable coordination complexes with transition metals has led to its use in catalysis and sensor development. For instance, researchers have reported the use of this compound as a ligand in metalloporphyrins for detecting trace amounts of heavy metals in environmental samples. Such applications underscore its versatility across multiple disciplines.

From an analytical standpoint, 5-bromo-3,4-dihydropyrimidin-4-one is often characterized using advanced spectroscopic techniques such as NMR and IR spectroscopy. These methods provide critical insights into its molecular structure and purity, ensuring its reliability as a starting material for downstream applications. Furthermore, computational modeling has become an invaluable tool for predicting its reactivity and stability under various reaction conditions.

Looking ahead, the continued exploration of 5-bromo-3,4-dihydropyrimidin-4-one is expected to yield new insights into its potential uses. Ongoing research is focused on optimizing its synthesis pathways and expanding its application scope into areas such as agrochemicals and diagnostics. As interdisciplinary collaboration between chemists and biologists intensifies, this compound is poised to play an even more significant role in advancing scientific innovation.

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