15018-56-1

Basic information

• Product Name: 5-BROMO-6-METHYLURACIL
• Synonyms: 5-BROMO-6-METHYLURACIL;TIMTEC-BB SBB003504;2,4(1H,3H)-Pyrimidinedione, 5-bromo-6-methyl-;5-Bromo-6-methyl-2,4(1H,3H)-pyrimidinedione;5-Bromo-6-methylpyrimidine-2,4-diol;Ai3-26570;Einecs 239-103-2;5-broMo-6-MethylpyriMidine
• CAS NO: 15018-56-1
• Molecular Formula: C₅H₅BrN₂O₂
• Molecular Weight: 205.01
• EINECS: 239-103-2
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 15018-56-1.mol

Chemical Properties

• Melting Point: 269-271 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.780±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.564
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.83±0.10(Predicted)
• CAS DataBase Reference: 5-BROMO-6-METHYLURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-6-METHYLURACIL(15018-56-1)
• EPA Substance Registry System: 5-BROMO-6-METHYLURACIL(15018-56-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 15018-56-1(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to white crystalline powder

InChI:InChI=1/C5H5BrN2O2/c1-2-3(6)4(9)8-5(10)7-2/h1H3,(H2,7,8,9,10)

Upstream product

• 626-48-2 6-Methyluracil 
• 33238-63-0 5-bromo-6-methyl-2-(methylthio)pyrimidin-4(3H)-one 
• 62459-19-2 5,5-dibromo-6-hydroxy-6-methyl-5,6-dihydrouracil 
• 6328-58-1 6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 1461-67-2 5-iodine-6-methyl-1H-pyrimidine-2,4-dione 
• 147-61-5 5-hydroxymethyl-6-methyluracil 
• 24048-74-6 1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinecarbaldehyde 

Downstream Products

• 56745-01-8 5-bromo-2,4-dichloro-6-methylpyrimidine 
• 591-07-1 acetylurea 
• 585-05-7 oxaluric acid 
• 144-62-7 oxalic acid 
• 54093-23-1 4-amino-5-bromo-2-chloro-6-methylpyrimidine 
• 3438-46-8 4-Methylpyrimidine 
• 13036-57-2 2-chloro-4-methylpyrimidine 
• 5424-21-5 2,4-dichloro-6-methylpyrimidine 
• 5541-07-1 4-methoxy-6-methylpyrimidine 
• 7752-70-7 5-bromo-2,4-dimethoxy-6-methylpyrimidine 
• 90904-99-7 5-[4-(4-cyanophenyl)-1-piperazinyl]-6-methyl-2,4(1H,3H)pyrimidinedione 
• 1450895-71-2 4-(benzyloxy)-5-bromo-6-methylpyrimidin-2(1H)-one 
• 1450895-73-4 5-bromo-6-methyl-4-(2-oxo-2-phenylethoxy)pyrimidin-2(1H)-one 
• 1150560-59-0 5-(2-fluoro-3-methoxyphenyl)-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methylpyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Chemical Properties of 6-Methyluracil-5-carbaldehyde Oxime

Oxidative chlorination of 6-methyluracil-5-carbaldehyde oxime in a two-phase system gave 7V-hydroxy-6-methyluracil-5-carboximidoyl chloride, and its bromination afforded ipso-substitution products, 5-bromo-6-methyluracil and 5,5-dibromo-6-hydroxy-6-methyl-5,6-dihydrouracil. The reaction of the title compound with acetic anhydride led to the formation of 6-methyluracil-5-carbonitrile or O-acetyl derivative, depending on the temperature. 7V-Hydroxy-6-methyluracyl-5-carboximidoyl chloride reacted with acetic acid at 100°C or with potassium iodide in boiling acetone to produce uracil-5-hydroxamic acid which was converted with high yields into the corresponding methyl ester and hydroximic acid amide. Quaternary ammonium salts were obtained by reactions of N-hydroxy-6-methyluracil-5-carboximidoyl chloride with pyridine and 1-methyl-1H-imidazole.

New access to thiazolo[4,5-d]pyrimidine derivatives

4-Amino-5-bromo-2-substituted-aminopyrimidines are readily obtained from the newly prepared 5-bromo-2,4-dichloro-6-methylpyrimidine by sequential treatment with ethanolic ammonia and secondary amines. These compounds were successfully reacted with various isothiocyanates in the presence of sodamide in DMF to form the new thiazolo[4,5-d] pyrimidine derivatives.

Halogenation and nitration of 1-carboxymethyl-5-methyluracil. Halophilic reaction involving acetic anhydride

1-Carboxymethyl-5-halo-6-hydroxy-5-methyl-5,6-dihydrouracils and 1-carboxymethyl-6-hydroxy-5-methyl-5-mtro-5,6-dihydrouracils were synthesized for the first time by oxidative halogenation and nitration of 1-carboxymethyl-5-methyluracil. Dihydrouracil derivatives bearing a Br atom at position C(5) and a hydroxy group at position C(6) treated with Ac2O undergo deoxyhalogenation.

Fe(III) and cobalt(II) coordination compounds of 5-bromo-6-methyl-2- morpholinepyrimidinium-4-amine pyridine-2,6-dicarboxylate

New coordination compounds, (bmmpaH)[Fe(pydc)2] (EtOH) 0.8(H2O)0.2 (1), (8QH)[Fe(pydc)2] H2O (2), (2ampyH)2[Mn(pydc)2] H2O (3), (2ampyH)[Cr(pydc)2](2ampy)0.5 H2O (4), [Co(H2O)5-μ (pydc)Co(pydc)] 2H2O (5), [Ni(pydcH)2] H2O (6), and [Cu(pydcH)2] (7), where bmmpa, 8Q, 2ampy, pydcH2 are 5-bromo-6-methyl-2-morpholinepyrimidine-4- amine, 8-hydroxyquinoline, 2-amino-6-methylpyridine, and pyridine-2,6- dicarboxylic acid, respectively, have been synthesized and structurally characterized by elemental analyses, infrared, UV spectroscopic methods, and X-ray crystallography. Metal ions of 1 and 5 are six-coordinate with distorted octahedral geometries. Compound 1 is an anionic mononuclear complex and 5 is a binuclear compound constructed from cationic and anionic parts. The crystal data of 5 reveal that the cationic part is formed by five terminal waters and one μ-carboxylate oxygen O2 from the anionic portion and the anionic complex is built from two deprotonated (pydc)2- moieties. In the compounds, pydcH2 is tridentate by one nitrogen of pyridine ring and two oxygens of carboxylate.

Electrophilic ipso-substitution in uracil derivatives

Treatment of 5-iodo-1,3,6-trimethyluracil with 50% H2SO 4 gives 1,3,6-trimethyluracil; with 5-bromo-1,3,6-trimethyluracil, a mixture of 1,3,6-trimethyluracil and 6-bromomethyl-1,3-dimethyluracil is obtained. 5-Chloro-1,3,6-trimethyluracil remains inert under these conditions. According to the DFT modeling of the reactions of 5-halo-1,3,6-trimethyluracils, a nucleophilic agent can abstract either Hal+ or the methyl proton from the carbocation formed by protonation of the starting halouracil at position 5, which accounts for the formation of two products from the 5-bromo derivative. Under similar conditions, 6-methyluracil dibromohydrin yields N-bromo-5-bromo-6-hydroxymethyluracil. Bromination or chlorination of 5-hydroxymethyl- or 5-formyl-6-methyluracils follows the ipso-substitution scheme leading to 6-methyluracil 5-halo- and 5,5-dihalohydrins.

Sulfur analogs of pyrimidine bases: Synthesis of 2-alkylthio- and 4-alkylthio-5-bromouracils and in silico evaluation of their biological activity

The general reactivity of alkylthiouracils under bromination conditions has been examined. Twenty 2-alkylthio- and 4-alkylthio-5-bromouracils of potential biological activity have been prepared. The structures of these compounds were confirmed by elementa

Oxidative halogenation of 6-methyluracil

An efficient method has been developed for the preparation of halo derivatives of 6-methyluracil by employing oxidative halogenation. Elemental halogens and potassium halides were used as the halogenating agents, while NaNO3 and H2O2 were used as the oxidizing agents. Iodination of 6-methyl-uracil leads to 5-iodo-6-methyluracil as the single reaction product, while bromination or chlorination lead to 5-halo-6-methyluracil, 5,5-dihalo-6-hydroxy-6-methyl-5,6-dihydrouracil, or their mixture depending on the acidity of the medium and the ratio of the substrate and reagents. Bromination of 5-chloro-6-methyluracil leads to 5-bromo-5-chloro-6-hydroxy-6-methyl-5,6-dihydrouracil, while chlorination of 6-methyl-, 5-bromo-6-methyl-, and 5-chloro-6-methyluracils using gaseous chlorine yields 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil.

A remarkably simple one-step procedure for the preparation of α-bromo-α,β-unsaturated carbonyl compounds

An easy and convenient one-step procedure for the conversion of α,β-unsaturated carbonyl compounds into their corresponding bromo-enones using NBS-Et3N·3HBr in the presence of potassium carbonate in dichloromethane at 0°C to room temperature under very mild conditions in high yields and significantly shorter times, is reported. Georg Thieme Verlag Stuttgart.

Hypervalent iodine in synthesis 91: A mild and efficient method for the halogenation of 6-methyluracil derivatives

The combined reagent of iodobenzene diacetate (or polymer-supported iodobenzene diacetate) with iodine or bromine was used as an effective halogenative agent of 6-methyluracil derivatives to the corresponding 5-halo-6-methyluracil derivatives at room temperature with high yields.

Diaminopyrimidines

Substituted-phenyl derivatives of 5-(1,4-piperazinyl)-2,4-pyrimidinediamine are effective as antibacterial and antitumor agents. Methods of preparing such compounds, pharmaceutical compositions based thereon, and a method of treating bacterial infections in a mammal in need of such treatment are disclosed.