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

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

Uses

Used in Pharmaceutical Industry:
2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYLis used as an intermediate in the synthesis of various pharmaceuticals. Its unique structure and functional groups contribute to the development of new drugs with potential therapeutic applications.
Used in Agricultural Industry:
In the agricultural sector, 2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYLis utilized as an intermediate in the production of fungicides and herbicides. Its chemical properties enable the creation of effective agents for controlling pests and diseases in crops, thereby enhancing agricultural productivity and crop protection.
Used in Chemical Industry:
2-PYRIMIDINAMINE, 5-BROMO-4-CHLORO-6-METHYLalso finds applications in the chemical industry due to its versatile nature. Its structural and functional properties make it suitable for various chemical reactions and processes, contributing to the development of new compounds and materials with diverse applications.

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

Upstream product

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

Discovery of new thienopyrimidine derivatives as potent and orally efficacious phosphoinositide 3-kinase inhibitors

A series of new thienopyrimidine derivatives has been discovered as potent PI3K inhibitors. The systematic SAR studies for these analogues are described. Among them, 8a and 9a exhibit nanomolar enzymatic potencies and sub-micromolar cellular anti-prolifer

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.

Protein Kinase Inhibitors

The present invention is directed to compounds of the Formula I as well as pharmaceutically acceptable salts, hydrates, isomers, or solvates thereof, wherein the variables are described herein. The present invention further relates to pharmaceutical compositions which comprise the compounds of Formula I, and to methods for inhibiting protein kinase and methods of treating diseases, such as cancers, inflammation.

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.

PYRIDO (2, 3-D) PYRIMIDIN0NE COMPOUNDS AND THEIR USE AS PI3 INHIBITORS

The present invention is directed to novel 4-methylpyridopyhmidinone compounds of Formula (I), and to salts thereof, their synthesis, and their use as inhibitors of phosphoinositide 3-kinase alpha (PI3- Ka).

Alkynylation of halo pyrimidines under Pd/C-copper catalysis: regioselective synthesis of 4- and 5-alkynylpyrimidines

5-Bromo-4-chloro-6-methylpyrimidines underwent facile Pd/C-Cu catalyzed coupling reactions with a variety of terminal alkynes, which resulted in the corresponding 4-alkynyl-5-bromopyrimidines, regioselectively, with good yields. 4-Chloro-5-iodo-6-methylpy