3993-80-4

Basic information

• Product Name: 4-chloro-5-iodopyriMidin-2-aMine
• Synonyms: 4-chloro-5-iodopyriMidin-2-aMine;5-Iodo-4-chloropyrimidin-2-amine
• CAS NO: 3993-80-4
• Molecular Formula: C4H3ClIN3
• Molecular Weight: 255.44419
• Mol File: 3993-80-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-chloro-5-iodopyriMidin-2-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-5-iodopyriMidin-2-aMine(3993-80-4)
• EPA Substance Registry System: 4-chloro-5-iodopyriMidin-2-aMine(3993-80-4)

Safety Data

• Hazardous Substances Data: 3993-80-4(Hazardous Substances Data)

Usage

General Description

4-chloro-5-iodopyrimidin-2-amine is a synthetic chemical compound with the molecular formula C4H3ClIN3. It is a heterocyclic compound containing a pyrimidine ring with a chlorine atom at position 4 and an iodine atom at position 5. The amine group is located at position 2 of the pyrimidine ring. 4-chloro-5-iodopyrimidin-2-amine has potential applications in the pharmaceutical and agrochemical industries, as it can be used as an intermediate in the synthesis of various bioactive molecules and pesticides. Its unique structure and properties make it a valuable building block for the development of new drugs and crop protection products. Additionally, its halogen substituents can impart desirable characteristics such as increased potency or selectivity in certain applications. Overall, 4-chloro-5-iodopyrimidin-2-amine is an important chemical intermediate with potential for diverse industrial applications.

Upstream product

• 3993-78-0 2-amino-4-chloropyrimidine 

Downstream Products

• 1425044-62-7 C₁₀H₈ClN₃ 
• 1425044-60-5 (S)-3-(1-((2-amino-5-iodopyrimidin-4-yl)amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 

Relevant articles and documents

Human Toll-like Receptor (TLR) 8-Specific Agonistic Activity in Substituted Pyrimidine-2,4-diamines

Activation of human toll-like receptor-8 (TLR8) evokes a distinct cytokine profile favoring the generation of Type 1 helper T cells. A multiplexed high-throughput screen had led to the identification of N4-butyl-5-iodo-6-methylpyrimidine-2,4-diamine as a pure TLR8 agonist, and a detailed structure-activity relationship study of this chemotype was undertaken. A butyl substituent at N4 was optimal, and replacement of the 5-iodo group with chloro, bromo, or fluoro groups led to losses in potency, as did the introduction of aromatic bulk. Drawing from our previous structure-based design, several 5-alkylamino derivatives were evaluated. Significant enhancement of potency was achieved in 5-(4-aminobutyl)-N4-butyl-6-methylpyrimidine-2,4-diamine. This compound potently induced Th1-biasing IFN-γ and IL-12 in human blood, but lower levels of the proinflammatory cytokines IL-1β, IL-6, and IL-8. These results suggest that the inflammatory and reactogenic propensities of this compound could be considerably more favorable than other TLR8 agonists under evaluation.

PYRIMIDINES AND USES THEREOF

The various examples presented herein are directed to compounds of the Formula: wherein R1-R5 are defined herein, and uses of such compounds to, among other things, inhibit an immune response in a subject.