14001-66-2

Basic information

• Product Name: 5-Bromo-2-methoxypyrimidine
• Synonyms: 5-BROMO-2-METHOXYPYRIMIDINE 97;Bromomethoxypyrimidine;2-Methoxy-5-bromopyrimidine;5-Bromo-2-methoxypyrimidine;5-Bromo-2-methoxy-1,3-diazine;5-Bromo-2-methoxypyrimidine 98%;2-Methoxy-5-broMopyriMidine(5-BroMo-2-MethoxypyriMidine);5-Bromo-22-methoxypyrimidine
• CAS NO: 14001-66-2
• Molecular Formula: C₅H₅BrN₂O
• Molecular Weight: 189.01
• EINECS: 1312995-182-4
• Product Categories: Pyrimidine;Alkoxy;Organohalides;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Heterocycle-Pyrimidine series
• Mol File: 14001-66-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 55.5-59.5 °C(lit.)
• Boiling Point: 259.8 °C at 760 mmHg
• Flash Point: 110.9 °C
• Appearance: White to yellow (may have pinkish tinge)/Solid
• Density: 1.628 g/cm³
• Vapor Pressure: 0.0205mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.22±0.22(Predicted)
• CAS DataBase Reference: 5-Bromo-2-methoxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-methoxypyrimidine(14001-66-2)
• EPA Substance Registry System: 5-Bromo-2-methoxypyrimidine(14001-66-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-43
• Safety Statements: 37/39
• WGK Germany: 3
• Hazardous Substances Data: 14001-66-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C5H5BrN2O/c1-9-5-7-2-4(6)3-8-5/h2-3H,1H3

Upstream product

• 67-56-1 methanol 
• 14001-67-3 5-bromo-2-methylthiopyrimidine 
• 124-41-4 sodium methylate 
• 32779-36-5 5-Bromo-2-chloropyrimidine 
• 38353-06-9 5-bromo-1H-pyrimidin-2-one 
• 32779-37-6 2,5-dibromopyrimidine 

Downstream Products

• 107166-90-5 (E)-methyl 3-(2-methoxy-5-pyrimidinyl)acrylate 
• 1083329-25-2 2,5-dibenzyloxypyrimidine 
• 1052686-60-8 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 
• 120717-41-1 2-methoxy-5-vinylpyrimidine 
• 101803-07-0 2-methoxy-5-(prop-1-yn-1-yl)pyrimidine 
• 1244037-16-8 propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide} 
• 1059705-07-5 2-methoxy-5-ethynylpyrimidine 
• 38373-47-6 2-methoxypyrimidine-5-carbonitrile 

Relevant articles and documents

Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

Discovery of potent and novel S-nitrosoglutathione reductase inhibitors devoid of cytochrome P450 activities

The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.

Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists

The discovery, synthesis, and optimization of compound 1 from a high-throughput screening hit to highly potent and selective peroxisome proliferator-activated receptor δ (PPARδ) agonists are reported. The synthesis and structure-activity relationship in this series are described in detail. On the basis of a general schematic PPAR pharmacophore model, scaffold 1 was divided into headgroup, linker, and tailgroup and successively optimized for PPAR activation using in vitro PPAR transactivation assays. A (2-methylphenoxy)acetic acid headgroup, a flexible linker, and a five-membered heteroaromatic center ring with two hydrophobic aryl substituents were required for efficient and selective PPARδ activation. The fine-tuning of these aryl substituents led to an array of highly potent and selective compounds such as compound 38c, displaying an excellent pharmacokinetic profile in mouse. In an in vivo acute dosing model, selected members of this array were shown to induce the expression of pyruvate dehydrogenase kinase-4 (PDK4) and uncoupling protein-3 (UCP3), genes that are known to be involved in energy homeostasis and regulated by PPARδ in skeletal muscle.