5-Bromo-2-iodopyrimidine CAS 183438-24-6

1. Preparation of vascular endothelial growth factor receptor 2 (VEGFR2) inhibitors
This is the most strategically valuable pharmaceutical use, without a doubt.
VEGFR2 is the core driving receptor for tumor angiogenesis, and inhibiting VEGFR2 can cut off the tumor's nutrient supply line, which is one of the most classic targets in the development of anti-tumor drugs. It is used to prepare pyrazine pyridine compounds, which are highly efficient VEGFR2 inhibitors.
The synthesis logic is clear: utilizing the high reactivity of iodine atoms, a pyrazine group is first introduced at position 2 through Suzuki coupling or Sonogashira coupling;

Reuse bromine atoms for a second round of coupling at position 5 to construct a complete pyrazinylpyridine skeleton. Two step reaction, completed in one go, with highly controllable product structure. The efficiency of this "one molecule, two-step coupling, one drug skeleton" cannot be achieved by mono halogenated pyrimidine intermediates.

2. Preparation of a novel conformational constrained glucagon receptor antagonist
Glucagon receptor antagonist is a new drug to treat type 2 diabetes and obesity. Traditional small molecule antagonists often have excessive flexibility and suffer from severe entropy loss when binding to receptors, resulting in insufficient efficacy.

The purpose of this direction is to provide a rigid pyrimidine core that locks the molecule in a specific conformation through dual site coupling, thereby significantly enhancing the binding affinity with glucagon receptors. Iodine and bromine atoms act as two independent connection points, allowing chemists to simultaneously introduce different pharmacophores at the 2nd and 5th positions of the pyrimidine ring, achieving a dual optimization of "conformational constraint+multi-point binding". This strategy has been validated in multiple preclinical candidate molecules.

3. Synthesis of anticancer drugs, analgesics, and other active molecules
Pyrimidine heterocycles themselves are the "privileged scaffold" in medicinal chemistry, widely present in anticancer drugs, antiviral drugs, and analgesics. As highly functionalized pyrimidine precursors, a large number of drug candidate molecules can be rapidly derived:
Anti cancer drug direction: Multiple kinase inhibitors can be synthesized by introducing aromatic, heteroaromatic, or amino groups at positions 2 and 5, respectively.

The nitrogen atom of the pyrimidine ring can form critical hydrogen bonds with the kinase hinge region, and the double substitution strategy can precisely regulate the selectivity and potency of the molecule.
Direction of analgesics: Pyrimidine derivatives are used in both nonsteroidal anti-inflammatory drugs and central analgesics, providing a shortcut for efficiently constructing such molecules.
Plant growth regulator: It can also be used to synthesize pesticide products such as fipronil and other plant growth regulators, which are of great significance for improving crop yield and quality and indirectly serving human health.

1. Pesticide intermediates
Pyrimidine heterocycles are one of the core skeletons in pesticide chemistry, widely used in the synthesis of herbicides, insecticides, and fungicides. As a universal intermediate for pharmaceuticals and pesticides, 5-bromo-2-iodopyrimidine is mainly used in the field of pesticides for:

Herbicide synthesis: Pyrimidine herbicides act by inhibiting acetyl lactate synthase (ALS) in plants.

New pyrimidine herbicide candidate molecules can be rapidly constructed through dual site substitution, providing structural diversity for herbicide variety innovation.

Pesticide synthesis: Pyrimidine insecticides can act on the nicotinic acetylcholine receptor (nAChR) of insects, and 5-bromo-2-iodopyrmidine is an efficient starting material for synthesizing such active molecules.
Currently, fluorinated/halogenated pesticides worldwide cover five major sectors: insecticides, fungicides, herbicides, acaricides, and plant growth regulators, with over a hundred varieties on the market and a compound annual growth rate of over 8%. Pyridine occupies an irreplaceable upstream position in this high-speed growth track due to its dual halogen orthogonal reactivity.

In basic organic chemistry research, 5-bromo-2-iodopyrmidine is often used as a model substrate for studying:

The reactivity sequence of halogens in palladium catalyzed coupling reaction (I>Br)
Optimization of Regional Selective Control Strategy
The competitive relationship between C-H bond activation and halogen substitution
The multiple chemical reaction sites (2-I, 5-Br, and two N atoms on the ring) in its structure make it an ideal model for studying the reactivity of multifunctional molecules.

According to product descriptions from multiple chemical companies, such as Zhende Chemical Technology, the application has been extended to the research and manufacturing of photoelectric conversion materials.

Pyrimidine ring is an excellent electron deficient heterocyclic ring with good electron transport ability.

The orthogonal reactivity of iodine and bromine also plays a key role here - introducing an electron donating group at one end and then an acceptor unit at the other end can precisely regulate the HOMO-LUMO energy level of the molecule and optimize the photoelectric conversion efficiency.
Although this direction is still in the early stages of development, multiple companies have already included it in their product application scope, indicating that market demand is emerging.

6.1 Dyes and pigment intermediates
Pyrimidine derivatives are widely used in azo dyes and fluorescent dyes. New pyrimidine based dyes can be synthesized by introducing chromophores through coupling reactions, providing high-performance colorants for industries such as textiles and printing.

6.2 Polymer Materials and Surfactants
Polymer materials containing pyrimidine rings have excellent thermal and chemical stability. It can be used as a bifunctional monomer to construct functional polymers containing pyrimidine units through stepwise coupling polymerization. In addition, pyrimidine surfactants have potential applications in special industrial scenarios due to their unique amphiphilicity and biocompatibility.