Overview and Chemical Properties

Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate is a halogenated pyrimidine derivative featuring a uracil (2,6-dioxo-1,2,3,6-tetrahydropyrimidine) core with a bromine substituent at position 5 and a methyl ester group at position 4. The combination of the electrophilic bromine and the activated ester makes this compound a versatile bifunctional synthon in organic and medicinal chemistry.

The 5-bromo substitution pattern on the uracil scaffold is well-recognized in nucleoside analogue research, as analogous halogenated uracil derivatives have been studied for their ability to participate in cross-coupling reactions (e.g., Suzuki, Heck, Sonogashira) and nucleophilic substitution, enabling access to diverse 5-substituted uracil libraries. The methyl ester at position 4 provides a handle for further elaboration via hydrolysis, amide coupling, or reduction.

Note: Molecular weight, exact CAS number, melting point, and purity specification should be confirmed against the product Certificate of Analysis (CoA) supplied with SKU M709807.

Safety and Handling

Before use, consult the Safety Data Sheet (SDS) for Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate (SKU M709807). As a reactive halogenated heterocycle, this compound should be treated as potentially irritating to skin, eyes, and the respiratory tract.

• Personal Protective Equipment (PPE): Wear chemical-resistant gloves, a laboratory coat, and safety goggles at all times when handling this compound.
• Ventilation: All weighing, dissolution, and reaction operations should be performed inside a well-ventilated chemical fume hood to minimize inhalation exposure.
• Storage: Store the reagent in a tightly sealed container in a cool (2–8 °C recommended until CoA confirms otherwise), dry, and dark location, away from incompatible materials such as strong oxidizers and bases.
• Waste Disposal: Dispose of waste according to local institutional and regulatory guidelines for halogenated organic compounds.

Always verify specific hazard classifications and first-aid measures in the product SDS prior to use.

Recommended Protocol: Solution Preparation and General Use

The following protocol outlines general procedures for preparing stock solutions and using Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate as a synthetic reagent. Adapt conditions to your specific application.

Materials Required

• Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate (SKU M709807)
• Anhydrous solvent suitable for intended reaction (e.g., DMF, DMSO, acetonitrile, or THF)
• Analytical balance (0.1 mg readability)
• Volumetric glassware
• Inert atmosphere equipment (Schlenk line or glovebox) if moisture-sensitive conditions are required

Stock Solution Preparation

1. Allow the reagent vial to equilibrate to room temperature before opening to prevent condensation of atmospheric moisture onto the solid.
2. Accurately weigh the required quantity of compound on an analytical balance inside a fume hood.
3. Transfer to an appropriate volumetric flask or vial and add the chosen anhydrous solvent. Stir or sonicate gently until fully dissolved.
4. For long-term storage of stock solutions, aliquot into sealed vials, purge with dry nitrogen or argon, and store at –20 °C (verify stability with CoA data).

Synthetic Applications

This reagent is suitable as a substrate for transition-metal-catalyzed cross-coupling reactions at the C5 bromine position (e.g., Pd-catalyzed Suzuki–Miyaura, Sonogashira, or Heck couplings) and for nucleophilic reactions at the ester carbonyl. Optimize catalyst loading, base, solvent, and temperature according to the specific transformation and relevant literature precedent.

Tip: Due to the acidity of the N–H protons in the uracil ring system, ensure that reaction conditions are compatible with the deprotonation state required for your transformation.

Quality Control and Troubleshooting

To ensure reproducible results when using Methyl 5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate, implement the following quality checks:

• Purity Verification: Confirm reagent purity by HPLC or NMR prior to use in sensitive reactions. Reference the CoA provided with SKU M709807 for expected purity values.
• Identity Confirmation: Verify compound identity using ¹H NMR and ¹³C NMR in a suitable deuterated solvent (e.g., DMSO-d₆). The expected signals include N–H proton resonances, methyl ester singlet, and absence of vinylic C5–H (replaced by Br).
• Moisture Sensitivity: If yield or purity is lower than expected, check that all solvents and glassware are rigorously dried, and that the reagent has been stored correctly.
• Reaction Monitoring: Use TLC (appropriate eluent system) or LC-MS to monitor reaction progress and confirm product formation.

If you encounter persistent issues with product quality or performance, contact Aladdin Scientific technical support with your batch number (found on the vial label and CoA).