1480-99-5

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl- (9CI)
• Synonyms: 5-fluoro-6-methyl-1H-pyrimidine-2,4-dione;5-fluoro-6-methyl-uracil;2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl- (9CI)
• CAS NO: 1480-99-5
• Molecular Formula: C5H5FN2O2
• Molecular Weight: 144.1038032
• Product Categories: PYRIMIDINE
• Mol File: 1480-99-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.42g/cm³
• Refractive Index: 1.511
• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl- (9CI)(1480-99-5)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl- (9CI)(1480-99-5)

Safety Data

• Hazardous Substances Data: 1480-99-5(Hazardous Substances Data)

Usage

General Description

2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl- (9CI) is a chemical compound with the molecular formula C5H4FN3O2. It is a heterocyclic organic compound that contains a pyrimidine ring with a fluorine atom at the 5-position and a methyl group at the 6-position. 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl- (9CI) is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential use as an anticancer and antiviral agent. 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-6-methyl- (9CI) is a versatile building block in organic synthesis and has potential applications in various fields, including medicine and agriculture.

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

Upstream product

• 1522-41-4 ethyl-2-fluoroacetoacetate 
• 57-13-6 urea 
• 626-48-2 6-Methyluracil 
• 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 articles and documents

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

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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.

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.