6153-44-2

Basic information

• Product Name: METHYL OROTATE
• Synonyms: 2,6-diketo-3H-pyrimidine-4-carboxylic acid methyl ester;2,6-dioxo-3H-pyrimidine-4-carboxylic acid methyl ester;6-Carbomethyoxyuracil;6-Methylcarboxyuracil;methyl 2,6-dihydroxy-4-pyrimidinecarboxylate;methyl 2,6-dioxo-3H-pyrimidine-4-carboxylate;METHYL OROTATE;RARECHEM AL BF 1310
• CAS NO: 6153-44-2
• Molecular Formula: C₆H₆N₂O₄
• Molecular Weight: 170.12
• EINECS: 228-171-9
• Mol File: 6153-44-2.mol

Chemical Properties

• Melting Point: 244 °C
• Boiling Point: 299.73°C (rough estimate)
• Appearance: Off-white to yellow or light brown/Powder
• Density: 1.5523 (rough estimate)
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.42±0.10(Predicted)
• CAS DataBase Reference: METHYL OROTATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL OROTATE(6153-44-2)
• EPA Substance Registry System: METHYL OROTATE(6153-44-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 6153-44-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL OROTATE is used as an intermediate in the synthesis of pyrimidine hydrazine acids for peptide recognition. Its role in this application is crucial for the development of new drugs and therapies that target specific peptide sequences.
Used in Chemical Synthesis:
METHYL OROTATE is also used in the preparation of pyrimidines bearing an acyclic moiety. This application is significant in the field of organic chemistry, as it allows for the creation of novel pyrimidine-based compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C6H6N2O4/c1-12-5(10)3-2-4(9)8-6(11)7-3/h2H,1H3,(H2,7,8,9,11)

Upstream product

• 67-56-1 methanol 
• 65-86-1 orotic acid 
• 80140-18-7 methyl N¹,N³-dibenzyloxymethyl-orotate 
• 74-88-4 methyl iodide 
• 3346-64-3 2,4-dioxo-1,2,3,4-tetrahydro-6-pyrimidinecarbonyl chloride 
• 6314-14-3 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid 
• 65-86-1 2,4-dihydroxypyrimidine-6-carboxylic acid 
• 616-38-6 carbonic acid dimethyl ester 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 26409-12-1 Orotic acid hydrazide 
• 769-97-1 Orotsaeure-amid 
• 144104-82-5 5-(2,6-Dichloro-phenyl)-1H-pyrimido[5,4-d][1,2]oxazine-2,4,8-trione 
• 4116-38-5 1,3-dimethylorotic acid 
• 13156-38-2 orotic acid butylamide 
• 6299-85-0 2,6-dichloropyrimidine-4-carboxylic acid methyl ester 
• 880091-40-7 methyl 6-(N'-benzyloxycarbonylhydrazino)-2-bromopyrimidine-4-carboxylate 
• 936476-63-0 methyl 2,6-dioxo-5-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate 
• 116393-71-6 5-iodo methyl orotate 
• 1254836-16-2 3-(benzyloxymethyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 
• 1254836-19-5 1-(2-(1H-pyrazol-1-yl)ethyl)-3-(benzyloxymethyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 
• 1254836-20-8 3-(benzyloxymethyl)-1-((3-ethyl-1,2,4-oxadiazol-5-yl)methyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 
• 1254836-18-4 3-(benzyloxymethyl)-2,6-dioxo-1-(pyridin-2-ylmethyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 
• 1254836-17-3 3-(benzyloxymethyl)-1-(2-morpholinoethyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid hydrochloride 

Relevant articles and documents

Synthesis and properties of PNA oligomers containing orotic acid derivatives

We have investigated the incorporation of C6-derivatives of uracil into polypyrimidine peptide nucleic acid oligomers (PNA). Starting with orotic acid (uracil-6-carboxylic acid) we have prepared a PNA monomer containing the methyl orotate nucleobase which is compatible with Fmoc-based synthesis. Treatment of the resin-bound oligomers with hydroxide or amines cleanly converted the ester to an orotic acid or orotamide-containing PNA. Alternatively, the methyl orotate-containing PNA was liberated from the resin by standard acidolysis. PNA bearing a modified nucleobase was found to hybridize to both poly(rA) and poly(dA). Complexes with poly(rA) were more stable than those with poly(dA) but both were destabilized relative to an unmodified PNA. Modification of a terminal residue was tolerated better than modification of an internal position. The type of charge provided by the modification affected the complex stability. In the worst case, an internal modification was nearly as detrimental as a base mismatch. Copyright Taylor & Francis, Inc.

A 6 - chloromethyl uracil synthetic method (by machine translation)

The invention discloses a 6 - chloromethyl uracil synthetic method, comprises the following steps: (1) esterification reaction: the orotic adding anhydrous in methanol, adds by drops two chlorine Asia sulphone, reaction 6 hours, to evaporate the solvent, the organic solvent is added, stirring at the room temperature, filtered, and dried to get the orotic acid methyl ester; (2) reduction reaction: the methyl orotic dissolved in methanol, added to the Lewis acid, adding sodium borohydride, stirring at room temperature for 12 - 16 hours, ice for acetic acid neutralization, to evaporate the solvent, the organic solvent is added, stirring at the room temperature, filtering, drying, be 6 - hydroxy methyl uracil; (3) chlorinated reaction: the 6 - hydroxy methyl uracil in the added to the organic solvent, by adding thionyl chloride and a catalytic amount of N, N - dimethyl formamide, reaction 2 hours, cooled to the room temperature, filtering, drying, be 6 - chloro methyl uracil. Synthesis method of the invention, avoids the use of toxic reagents, mild reaction conditions, cheap, high yield, and is favorable for industrial production. (by machine translation)

Preparation method of 5-chloro-6-chloromethyluracil

The invention provides a 5-chloro-6-chloromethyl-uracil and a preparation method thereof. The method comprises the following steps: esterifying the 6-position carboxylic acid of orotic acid used as an initial raw material, chlorinating the 5-position hydrogen, reducing the 6-position ester into a hydroxymethyl group, and carrying out a chlorination substitution reaction to obtain the target product. The preparation method has the advantages of simplicity in operation, stable process, high yield and low cost, and is suitable for industrial production.

Synthesis of orotidine by intramolecular nucleosidation

An intramolecular nucleosidation approach provides easy access to orotidine in high yields. Notably, orotate itself is used as a leaving group at the anomeric position. This method has the potential for facile access to derivatives of orotidine of therapeutic interest, with implications for prebiotic formation of nucleosides. This journal is

METHOD OF CONTROLLING UNDESIRED VEGETATION

The present invention relates to methods of controlling undesired plant growth in crops of soya through the use of certain substituted pyrimidine derivatives. It also relates to certain novel substituted pyrimidine derivatives. Effective weed control is thereby obtained, whilst at the same time achieving unexpected levels of crop safety.

A novel route to 2,4-dianilino-substituted pyrimidines

A method is described to couple sterically-hindered electron-poor anilines to the 4-position of the pyrimidine core using a pyrimidine-2,4-bis(trifluoromethanesulfonate).

PYRIMIDINE DERIVATIVES AND THEIR USE AS HERBICIDES

The present invention relates to substituted pyrimidine derivatives, as well as N- oxides thereof and agriculturally acceptable salts thereof, and their use to control undesired plant growth, in particular in crops of useful plants. The invention extends to herbicidal compositions comprising such compounds, N-oxides and/or salts as well as mixtures of the same with one or more further active ingredient (such as, for example, an herbicide, fungicide, insecticide and/or plant growth regulator) and/or a safener. The invention further relates to intermediates useful in the preparation of such compounds, and to processes for their preparation.

CHEMICAL COMPOUNDS

The present invention relates to substituted pyrimidine derivatives of as well as N-oxides and agriculturally acceptable salts thereof, and their use to control undesired plant growth, in particular in crops of useful plants. The invention extends to herbicidal compositions comprising such compounds, N-oxides and/or salts as well as mixtures of the same with one or more further active ingredient (such as, for example, an herbicide, fungicide, insecticide and/or plant growth regulator) and/or a safener.

CHEMICAL COMPOUNDS

The present invention relates to substituted pyrimidine derivatives as well as N- oxides and agriculturally acceptable salts thereof, and their use to control undesired plant growth, in particular in crops of useful plants. The invention extends to herbicidal compositions comprising such compounds, N-oxides and/or salts as well as mixtures of the same with one or more further active ingredient (such as, for example, an herbicide, fungicide, insecticide and/or plant growth regulator) and/or a safener.

Synthesis of substituted pyrimidine hydrazine acids (PHA) and their use in peptide recognition

Substituted pyrimidine-hydrazine-acids (PHA) were prepared from orotic acid in five synthetic steps and high yields. Their geometry of hydrogen bond acceptor and donor sites make them suitable for the molecular recognition of peptide β-sheets. In non-protic solvents the PHA unit emits at around 420 nm after irradiation at 281 nm. The emission intensity decreases upon peptide binding and signals the binding event. Peptides consisting of PHAs and natural amino acids or a turn structure motif were prepared. The investigation of the intramolecular binding pattern by NMR spectroscopy revealed the expected interaction of the PHA and peptide β-sheet.