56686-16-9

Basic information

• Product Name: 5-BROMO-2,4-DIMETHOXYPYRIMIDINE
• Synonyms: 5-BROMO-2,6-DIMETHOXYPYRIMIDINE;5-BROMO-2,4-DIMETHOXYPYRIMIDINE;Bromo-2,4-dimethoxypyrimidine;5-BROMO-2,4-DIMETHOXYPYRIMIDINE 97+%;5-BROMO-2,4-DIMETHOXPYRIMIDINE;Nsc81442;2,4-DiMethoxy-5-broMopyriMidine;5-BroMo-2,4-bis(Methyloxy)pyriMidine
• CAS NO: 56686-16-9
• Molecular Formula: C₆H₇BrN₂O₂
• Molecular Weight: 219.04
• Product Categories: Pyrimidine;Alkoxy;Organohalides;Nucleotides and Nucleosides;5-FOA;Bases & Related Reagents;Nucleotides;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Building Blocks;C6 to C8;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyrimidine series
• Mol File: 56686-16-9.mol

Chemical Properties

• Melting Point: 62-65 °C(lit.)
• Boiling Point: 125 °C / 17mmHg
• Flash Point: 133.4 °C
• Appearance: White to pale yellow/Powder or Crystalline Powder
• Density: 1.563 g/cm³
• Vapor Pressure: 0.00245mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetone, Dichloromethane
• PKA: 1.27±0.29(Predicted)
• CAS DataBase Reference: 5-BROMO-2,4-DIMETHOXYPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2,4-DIMETHOXYPYRIMIDINE(56686-16-9)
• EPA Substance Registry System: 5-BROMO-2,4-DIMETHOXYPYRIMIDINE(56686-16-9)

Safety Data

• Hazard Codes: Xi,Xn
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 56686-16-9(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

InChI:InChI=1/C6H7BrN2O2/c1-10-5-4(7)3-8-6(9-5)11-2/h3H,1-2H3

Upstream product

• 36082-50-5 2,4-dichloro-5-bromopyrimidine 
• 124-41-4 sodium methylate 
• 123551-48-4 5-Acetoxymercuri-2,4-dimethoxypyrimidine 
• 67-56-1 methanol 
• 3551-55-1 2,4-dimethoxypyrimidine 
• 123551-51-9 5,5'-Mercuri-bis-(2,4-dimethoxypyrimidine) 

Downstream Products

• 936250-17-8 2,4‐dimethoxy‐5‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)pyrimidine 
• 794521-24-7 (2,4-dimethoxy-5-pyrimidinyl)-(4-ethylphenyl) methanol 
• 1023754-47-3 (tert-butyldimethylsilanyl)(2,4-dimethoxypyrimidin-5-yl)(3,4,5-trimethoxyphenyl)amine 
• 5151-34-8 2,4-Dimethoxy-5-methylpyrimidine 
• 1101167-59-2 4-(2,4-dimethoxypyrimidin-5-yl)benzonitrile 
• 60186-89-2 4-bromo-2,6-dimethoxy-pyrimidine 
• 1335213-01-8 2,4-dimethoxy-5-(4-methoxyphenyl)pyrimidine 
• 89641-18-9 2,4-dimethoxypyrimidin-5-ylboronic acid 
• 1423122-46-6 p-tolyl(4-bromo-2,6-dimethoxy-5-pyrimidineyl)methanone 
• 1423122-41-1 phenyl(4-bromo-2,6-dimethoxy-5-pyrimidineyl)methanone 
• 110821-05-1 5-(2,4-dimethoxypyrimidinyl)-1-phenylmethanol 
• 1423122-48-8 C₁₆H₁₄N₂O₃ 
• 1423122-39-7 C₁₅H₁₂N₂O₃ 
• 1423122-47-7 p-tolyl(4-(trimethylsilylethynyl)-2,6-dimethoxy-5-pyrimidineyl)methanone 

Relevant articles and documents

Synthesis and biological evaluation of novel flexible nucleoside analogues that inhibit flavivirus replication in vitro

Flaviviruses, such as Dengue (DENV) and Zika (ZIKV) viruses, represent a severe health burden. There are currently no FDA-approved treatments, and vaccines against most flaviviruses are still lacking. We have developed several flexible analogues (“fleximers”) of the FDA-approved nucleoside Acyclovir that exhibit activity against various RNA viruses, demonstrating their broad-spectrum potential. The current study reports activity against DENV and Yellow Fever Virus (YFV), particularly for compound 1. Studies to elucidate the mechanism of action suggest the flex-analogue triphosphates, especially 1-TP, inhibit DENV and ZIKV methyltransferases, and a secondary, albeit weak, effect on the DENV RNA-dependent RNA polymerase was observed at high concentrations. The results of these studies are reported herein.

Bromination of pyrimidines: A simple inexpensive method

Although the introduction of halogens into the pyrimidine ring has been accomplished numerous times, the methods usually involve either specialised reagents or very aggressive conditions. This communication paper describes the introduction of bromine into position 5 of the pyrimidine ring using common inorganic salts at room temperature. An evaluation of the substituents required for successful reaction is provided.

Metallation of 2,4-dialkoxy-5-bromopyrimidine and formylation with dimethylformamide: Isolation of 2,6-dialkoxy-5-dimethylaminopyrimidine-4- carboxaldehyde

Direct metallation of 2,4-dialkoxy-5-bromopyrimidine with lithium diisopropylamide and consequent trapping by dimethylformamide resulted unexpectedly in the formation of 2,6-dialkoxy-5-dimethylaminopyrimidine-4- carboxaldehyde via displacement of bromine by dimethylamine moiety of dimethylformamide. Copyright

Oxidative amination of cuprated pyrimidine and purine derivatives

Using regioselective cuprations (via magnesiations), various primary, secondary and tertiary aminated pyrimidine and purine derivatives were prepared by the oxidative coupling of lithium amidocuprates using chloranil. DNA and RNA units such as aminated uracil or thymine, and adenine, as well as a CDK inhibitor, purvalanol A, were all obtained under mild conditions and satisfactory yields.

AZABICYCLO [3. 1. 0] HEXYL DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS

The present invention relates to novel compounds of formula (I)' or a salt thereof: wherein G is selected from a group consisting of: phenyl, a 5- or 6-membered monocyclic heteroaryl group, or a 8- to 11 -membered heteroaryl bicyclic group; A is a group P

NOVEL SYNTHESIS OF 5-HALOURACILS FROM 5-MERCURI-2,4-DIMETHOXYPYRIMIDINES

Direct C-mercuration of 2,4-dimethoxypyrimidine with mercury (II) acetate has been shown to give the 5-mercuri-derivative, which is readily converted, either directly or via 5,5'-mercuribis (2,4-dimethoxypyrimidine), into the 5-halo derivatives.Hydrolysis of the latter with hydrochloric acid affords the 5-halouracils.