6314-12-1

Basic information

• Product Name: 2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYL-
• Synonyms: 2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYL-;5-Bromo-4-chloro-6-methylpyrimidin-2-amine;2-Amino-5-bromo-4-chloro-6-methylpyrimidine;5-Bromo-4-chloro-6-methyl-2-pyrimidinamine;NSC 40200
• CAS NO: 6314-12-1
• Molecular Formula: C₅H₅BrClN₃
• Molecular Weight: 222.473
• Mol File: 6314-12-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 390.4°Cat760mmHg
• Flash Point: 189.9°C
• Appearance: /
• Density: 1.815
• Vapor Pressure: 2.65E-06mmHg at 25°C
• Refractive Index: 1.638
• CAS DataBase Reference: 2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYL-(6314-12-1)
• EPA Substance Registry System: 2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYL-(6314-12-1)

Safety Data

• Hazardous Substances Data: 6314-12-1(Hazardous Substances Data)

Usage

General Description

5-Bromo-4-chloro-6-methyl-2-pyrimidinamine is a chemical compound with the molecular formula C6H5BrClN3. It is a heterocyclic compound that contains a pyrimidine ring with a bromine, chlorine, and methyl group attached to it. 2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYL- is commonly used as an intermediate in the synthesis of pharmaceuticals, specifically in the production of fungicides and herbicides. Its structural and functional properties make it suitable for various applications in the chemical industry. Overall, 5-bromo-4-chloro-6-methyl-2-pyrimidinamine is a versatile compound with potential uses in pharmaceutical and agricultural industries.

InChI:InChI=1/C5H5BrClN3/c1-2-3(6)4(7)10-5(8)9-2/h1H3,(H2,8,9,10)

Upstream product

• 3977-29-5 2-amino-6-methyl-3H-pyrimidin-4-one 
• 5600-21-5 2-amino-6-methyl-4-chloropyrimidine 
• 6307-35-3 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one 

Downstream Products

• 7781-30-8 5-bromo-6-methyl-N⁴-phenyl-pyrimidine-2,4-diamine 
• 6633-70-1 5-bromo-N⁴-(4-bromo-phenyl)-6-methyl-pyrimidine-2,4-diamine 
• 1013099-50-7 5-bromo-4-chloro-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidine 
• 1013099-51-8 trans-4-{[5-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-yl]amino}cyclohexanol 

Relevant articles and documents

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.

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.

Design and synthesis of a novel pyrrolidinyl pyrido pyrimidinone derivative as a potent inhibitor of PI3Kα and mTOR

Lead optimization efforts that employed structure base drug design and physicochemical property based optimization leading to the discovery of a novel series of 4-methylpyrido pyrimidinone (MPP) are discussed. Synthesis and profile of 1, a PI3Kα/mTOR dual inhibitor, is highlighted.