Production Method 1

1635-28-5

959240-54-1

Reaction Conditions

1.1 Reagents: Phosphoric tribromide Solvents: Acetonitrile ;  1 h, reflux; reflux → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized

Reference

Preparation of substituted benzamide compounds for treating conditions mediated at least in part via the bradykinin 1 receptor

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4-Bromo-N,N-dimethylpyrimidin-2-amine Raw materials

• 2-(dimethylamino)pyrimidin-4-ol

4-Bromo-N,N-dimethylpyrimidin-2-amine Preparation Products

• 4-Bromo-N,N-dimethylpyrimidin-2-amine (959240-54-1)

• 1. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 2. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 3. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
• 4. Evolution of dealloying induced strain in nanoporous gold crystals?
  Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693
• 5. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389

• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Introduction to 4-Bromo-N,N-dimethylpyrimidin-2-amine (CAS No. 959240-54-1)

4-Bromo-N,N-dimethylpyrimidin-2-amine, identified by its Chemical Abstracts Service (CAS) number 959240-54-1, is a significant compound in the realm of pharmaceutical and agrochemical research. This heterocyclic amine derivative has garnered attention due to its versatile structural framework, which makes it a valuable intermediate in the synthesis of various biologically active molecules. The presence of both bromine and amine functional groups provides unique reactivity, enabling diverse chemical modifications that are pivotal for drug discovery and material science applications.

The compound belongs to the pyrimidine class of nitrogen-containing heterocycles, which are ubiquitous in natural products and pharmacologically relevant molecules. Pyrimidines serve as the backbone for several essential biological processes, including DNA and RNA synthesis. Consequently, derivatives of pyrimidine have been extensively explored for their potential therapeutic effects against a wide range of diseases, such as cancer, infectious diseases, and metabolic disorders.

In recent years, 4-Bromo-N,N-dimethylpyrimidin-2-amine has been employed in the development of novel therapeutic agents. Its brominated pyrimidine core is particularly useful in constructing kinase inhibitors, which are critical in targeted cancer therapies. For instance, studies have demonstrated its role as a precursor in synthesizing small-molecule inhibitors that selectively target aberrant signaling pathways in oncogenic cells. The dimethylamino group enhances lipophilicity, improving membrane permeability and bioavailability—key factors for drug efficacy.

Moreover, the amine functionality allows for further derivatization through coupling reactions with carboxylic acids or aldehydes via amide or urea bond formation. This flexibility has been exploited in designing peptidomimetics and protein-protein interaction modulators. Recent advancements in medicinal chemistry have highlighted its utility in generating inhibitors of bacterial enzymes, addressing the growing challenge of antibiotic resistance. The bromine atom serves as a handle for cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, facilitating the introduction of aryl or heteroaryl groups into the molecule.

The agrochemical sector has also benefited from 4-Bromo-N,N-dimethylpyrimidin-2-amine, where it is used to develop novel herbicides and fungicides. Its structural motif is reminiscent of established agrochemicals that disrupt essential metabolic pathways in weeds and fungi. Researchers have leveraged computational modeling to identify analogs with enhanced selectivity and reduced environmental impact. These efforts align with global initiatives to promote sustainable agriculture by minimizing chemical residues.

From a synthetic chemistry perspective, 4-Bromo-N,N-dimethylpyrimidin-2-amine exemplifies the importance of functional group interplay in designing molecular frameworks with tailored properties. The bromine atom facilitates metal-catalyzed transformations, while the amine group participates in nucleophilic additions or condensations. This duality has enabled the rapid assembly of complex scaffolds through multi-step synthetic routes. Techniques such as microwave-assisted synthesis have been applied to optimize reaction conditions, enhancing yield and purity—crucial considerations for industrial-scale production.

The compound’s role in material science is equally noteworthy. Pyrimidine derivatives exhibit interesting electronic properties due to their conjugated systems and nitrogen lone pairs. 4-Bromo-N,N-dimethylpyrimidin-2-amine has been investigated as a building block for organic semiconductors and light-emitting diodes (OLEDs). Its ability to form stable π-stacking interactions makes it suitable for designing supramolecular assemblies with applications in optoelectronics and nanotechnology.

Regulatory considerations play a crucial role in the commercialization of 4-Bromo-N,N-dimethylpyrimidin-2-amine. Manufacturers must adhere to Good Manufacturing Practices (GMP) to ensure consistency and safety during production. Additionally, environmental impact assessments are conducted to evaluate potential ecotoxicological risks associated with its use. These measures underscore the commitment to responsible chemical stewardship within the industry.

Future research directions may explore its potential as a chiral auxiliary or catalyst ligand due to its rigid pyrimidine core and tunable electronic properties. Advances in asymmetric synthesis could unlock new opportunities for enantioselective drug development. Furthermore, interdisciplinary approaches combining computational chemistry with experimental validation are expected to accelerate the discovery pipeline for novel derivatives.

In conclusion,4-Bromo-N,N-dimethylpyrimidin-2-amine (CAS No. 959240-54-1) is a multifaceted compound with broad applications across pharmaceuticals, agrochemicals, and materials science. Its unique structural features enable diverse functionalization strategies, making it indispensable for synthetic chemists pursuing innovative molecular architectures. As research continues to uncover new possibilities, this compound will remain at the forefront of scientific exploration.

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