1480-99-5

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl(9CI) is used as an intermediate in the synthesis of pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl(9CI) serves as an intermediate for the production of various agrochemicals, contributing to the development of effective pest control and crop protection solutions.
Used in Anticancer Research:
2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl(9CI) has been studied for its potential use as an anticancer agent. Its unique chemical properties may contribute to the development of novel treatments for various types of cancer.
Used in Antiviral Research:
2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl(9CI) has also been investigated for its potential as an antiviral agent. Its ability to interact with viral components could lead to the development of new antiviral therapies to combat various viral infections.

InChI:InChI=1/C5H5FN2O2/c1-2-3(6)4(9)8-5(10)7-2/h1H3,(H2,7,8,9,10)

Upstream product

• 626-48-2 6-Methyluracil 
• 1522-41-4 ethyl-2-fluoroacetoacetate 
• 57-13-6 urea 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 108195-40-0 5-Fluoro-2-methoxy-6-methyl-3H-pyrimidin-4-one 
• 705-50-0 2-ethylmercapto-5-fluoro-6-methyl-3H-pyrimidin-4-one 

Downstream Products

• 954220-98-5 2,4-dichloro-5-fluoro-6-methyl-pyrimidine 
• 64582-50-9 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-fluoro-6-methyluracil 
• 175354-57-1 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-fluoro-6-methyluracil 

Relevant academic research and scientific papers

Electrophilic fluorination of 6-methyl- and 1,3,6-trimethyluracils in water

The reaction of 4-chloromethyl-1-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) with 6-methyl- and 1,3,6-trimethyluracil in water has been studied. According to the kinetic data, the fluorination follows a bimolecular mechanism with intermediate formation of cationic σ-complexes.

Promotional effect of ionic liquids in electrophilic fluorination of methylated uracils

A novel efficient protocol has been developed for fluorination of methylated uracils involving a stoichiometric amount of ionic liquid (IL) in alcohols. The fluorination of 6-methyluracil and 1,3,6-trimethyluracil has been carried out using the electrophilic fluorinating reagent Selectfluor (F-TEDA-BF4) in MeOH and EtOH solvents with the formation of 5-fluoro-6-methyluracil, 5-fluoro-1,3,6-trimethyluracil as well as α-fluoromethoxy- and α-fluoroethoxy ethers of difluorodihydrouracils as the main products. The use of a stoichiometric amount of ionic liquid as an additive results in acceleration of the reaction. It has been found that the effect of the anion of the IL on the rate of the reaction is more pronounced compared to that of the cation, the effectiveness of the anions decreasing in the following order: [HSO4-] > [OTf-] ～ [NTf2-] > [BF4-] > [PF6-]. The influence of metal carbonates on the yields of fluorouracils has also been evaluated.

Synthesis method of 2-chloro-5-fluoro-6-methylpyrimidine

The invention relates to a synthesis method of 2-chloro-5-fluoro-6-methylpyrimidine, which comprises the following steps: dissolving sodium methoxide in methanol, adding urea, stirring, dropwisely adding ethyl 2-fluoroacetoacetate, and carrying out a reflux reaction for 2-3 hours to obtain an intermediate A; mixing the intermediate A, phosphorus oxychloride and organic alkali according to a weightratio of 1: (5-10): (0.3-2) for reaction, cooling the mixture, removing redundant phosphorus oxychloride, adding water for quenching extraction, drying, and concentrating to obtain a product B; and adding ethanol, zinc powder and acetic acid into the product B, carrying out a heating reflux reaction for 10-16 hours, cooling, filtering, evaporating to remove the ethanol, extracting with an organicsolvent, evaporating to dryness to obtain a crude product, and carrying out vacuum distillation to obtain a pure product C, namely the 2-chloro-5-fluoro-6-methylpyrimidine. The method has the effectsthat the yield is increased, the time is shortened, the operation is simple, and the post-treatment process is simplified.

6-Substituted and 5,6-disubstituted derivatives of uridine: Stereoselective synthesis, interaction with uridine phosphorylase, and in vitro antitumor activity

Stereoselective procedures are described for the synthesis of 6- alkyluridines by Lewis acid-catalyzed condensation of (a) trimethylsilylated 6-alkyl-4-alkylthiouracils with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D- ribofuranose (ABR) and (b) trimethylsilylated 6-alkyl-3-benzyluracils with ABR. The 4-methylthio group was subsequently removed with the use of 1 N trifluoroacetic acid and the 3-benzyl group by a new modified procedure with the use of the complex BBr3-THF. Furthermore, 6-(hydroxymethyl)uridine (39) and 5-fluoro-6-(hydroxymethyl)uridine (40) were obtained by sequential oxidation with SeO2 and reduction with tetrabutylammonium borohydride of the 6-methyl group of 6-methyluridine (5) and 5-fluoro-6-methyluridine (35), and their corresponding 6-fluoromethyl congeners 41 and 42 were obtained by DAST treatment of 39 and 40, respectively. For all the foregoing nucleosides in the fixed syn conformation about the glycosyl bond, 1H NMR spectroscopy further demonstrated that the pentose rings exist predominantly in the conformation N (3'-endo). Most of the nucleosides were weak substrates of Escherichia coli pyrimidine nucleoside phosphorylase. Enhanced susceptibility to phosphorolysis was exhibited by two of them, 39 and 41, with 6-CH2OH and 6-CH2F substituents capable of formation of an additional hydrogen bond with the enzyme. The 5-fluoro-6-substituted uridines were the poorest substrates. Cytotoxicities of the nucleosides were examined vs the human tumor cell lines MOLT-3, U-937, K-562, and IM-9, as well as PHA-stimulated human lymphocytes. Two of the analogues, 5-fluoro-6-(fluoromethyl)uridine (42) and 5-fluoro-6- (hydroxymethyl)uridine (40), exhibited cytotoxicities comparable to that of 5-fluorouracil.

Process for fluorinating uracil and derivatives thereof

Direct fluorination of uracil and its derivatives, in the presence of an aqueous solvent, by fluorine gas to produce 5-fluorouracil and 5-fluorouracil derivatives is disclosed. Novel compounds produced by the reaction, such as 5,5-difluoro-6-hydroxy-5,6-dihydrouracil are also disclosed. The derivatives of 5-fluorouracil are useful as germicidal agents while 5-fluorouracil itself is a known cancer chemotherapy agent.