Methyl 5-Bromo-2,6-Dioxo-1,2,3,6-Tetrahydropyrimidine-4-Carboxylate
Methyl 5-Bromo-2,6-Dioxo-1,2,3,6-Tetrahydropyrimidine-4-Carboxylate
Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate is a halogenated uracil-derived pyrimidine building block widely employed in medicinal chemistry and heterocyclic synthesis as a versatile electrophilic intermediate.
- Chemical Name
- Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
- Core Scaffold
- Pyrimidine-2,6(1H,3H)-dione (uracil-type)
- Functional Groups
- C5 bromine substituent, ester (methyl carboxylate) at C4, two lactam carbonyls
- Primary Research Use
- Electrophilic synthetic intermediate for cross-coupling, nucleophilic substitution, and heterocycle elaboration
- Available SKU
- M709807
- Supplier
- Aladdin Scientific
Chemical Identity and Structural Features
Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate belongs to the family of 2,6-dioxopyrimidines, which are structurally related to uracil—a naturally occurring nucleobase. The compound carries three key functional handles: (1) a bromine atom at the C5 position of the pyrimidine ring, (2) a methyl ester group at C4, and (3) two carbonyl groups at C2 and C6 that form the characteristic dioxo (uracil-like) motif.
The C5 carbon–bromine bond imparts significant electrophilicity, making this position highly reactive toward palladium-catalysed cross-coupling reactions (e.g., Suzuki–Miyaura, Sonogashira) as well as metal–halogen exchange sequences. The methyl ester at C4 provides an additional electrophilic centre susceptible to nucleophilic attack (aminolysis, transesterification) or further transformation to aldehydes, alcohols, or carboxylic acids under appropriate conditions.
Together, these features make the molecule a multi-functional scaffold for the construction of structurally diverse pyrimidine analogues relevant to drug discovery and materials research.
Applications in Synthesis and Drug Discovery
Halogenated pyrimidine-dione derivatives such as this compound are recognised as privileged building blocks in medicinal chemistry. The uracil-type core is a bioisostere commonly found in antiviral, anticancer, and enzyme-inhibitor scaffolds. Introduction of substituents at C5 via the reactive C–Br bond allows rapid diversification of the core for structure–activity relationship (SAR) studies.
Typical synthetic applications include:
- Palladium-catalysed cross-coupling: The C5–Br bond participates in Suzuki–Miyaura (with aryl/vinyl boronic acids), Sonogashira (with terminal alkynes), and Stille couplings to install aryl, vinyl, or alkynyl groups.
- Nucleophilic aromatic substitution and amination: Under appropriate conditions, displacement of the halide or functionalisation of the ester enables access to aminopyrimidine and carboxamide derivatives.
- Heterocycle annulation: The 1,3-diNH sites and the ester can serve as handles for ring-closure reactions to form fused bicyclic systems.
- Fragment-based drug design: The compact, polar fragment profile of this compound makes it suitable for fragment screening libraries targeting nucleotide-binding enzymes.
These versatile reaction pathways position Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate as a high-value intermediate for both academic and industrial research programmes.
Handling, Storage, and Safety Considerations
As with most organobromine heterocyclic intermediates, appropriate laboratory safety precautions should be observed when working with Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate. Researchers should consult the product Safety Data Sheet (SDS) prior to use for authoritative hazard, first-aid, and disposal information specific to this compound.
General guidelines include:
- Personal protective equipment (PPE): Wear appropriate gloves (nitrile or equivalent), a laboratory coat, and eye protection. Work in a well-ventilated area or a fume hood when weighing or dissolving the material.
- Storage: Store in a cool, dry location away from light and moisture. Seal the container tightly after each use to prevent hydrolysis of the ester group and degradation of the compound. Specific temperature requirements should be confirmed from the product label or SDS.
- Waste disposal: Dispose of all waste in accordance with local institutional and regulatory guidelines for halogenated organic compounds.
- Incompatibilities: Avoid contact with strong bases (which may promote ester hydrolysis or ring-opening) and strong oxidising agents.
Always verify current safety information directly from the Aladdin Scientific product page or the accompanying SDS before beginning experiments.
Ordering Information
Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate is available from Aladdin Scientific under SKU M709807. Researchers and procurement teams are encouraged to contact Aladdin Scientific for current pricing, available pack sizes, purity specifications, and lead times. Custom quantities or bulk orders may be accommodated upon request.
To place an order or request a quote, visit the product page on the Aladdin Scientific website or contact your regional sales representative.
Frequently asked questions
What is Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate used for?
This compound is primarily used as a synthetic building block in medicinal chemistry and heterocyclic synthesis. The reactive C5–bromine bond enables palladium-catalysed cross-coupling reactions (e.g., Suzuki–Miyaura, Sonogashira), while the methyl ester at C4 provides a site for further functionalisation, enabling access to diverse pyrimidine-dione derivatives for drug discovery and SAR studies.
How should this compound be stored to maintain stability?
The compound should be stored in a cool, dry environment away from light and moisture. Containers should be tightly sealed after each use to prevent hydrolysis of the methyl ester and degradation of the pyrimidine ring. Please refer to the product label and SDS from Aladdin Scientific for confirmed storage temperature requirements.
What reactions can be performed at the C5 bromine position?
The C5–Br bond is compatible with several key transformations including Suzuki–Miyaura cross-coupling with boronic acids, Sonogashira coupling with terminal alkynes, Stille coupling with organostannanes, and metal–halogen exchange for organolithium or organomagnesium chemistry. These reactions allow efficient introduction of aryl, vinyl, alkynyl, and other carbon-based substituents onto the pyrimidine scaffold.
Where can I purchase Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate?
This compound is available from Aladdin Scientific under product SKU M709807. Visit the Aladdin Scientific website or contact your regional sales representative to request pricing, availability, and pack size information.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley, 5th ed. General reference for nucleophilic substitution and ester chemistry principles.
- Negishi, E. (Ed.) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley-Interscience. General reference for palladium-catalysed cross-coupling reactions including Suzuki–Miyaura and Sonogashira couplings.
- Brown, D. J. The Pyrimidines. Wiley-Interscience (The Chemistry of Heterocyclic Compounds series). General reference for pyrimidine and uracil derivative chemistry.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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