3013-92-1

Usage

Uses

Used in Pharmaceutical Industry:
5-FLUORO-1,3-DIMETHYLURACIL is used as a starting material for the synthesis of various compounds with potential pharmaceutical applications. Its unique chemical structure allows for the development of new drugs and therapeutic agents.
1. As a starting material for the regioselective synthesis of tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones, which are compounds with potential applications in the treatment of various diseases, including cancer.
2. To synthesize 5-bis(ethoxycarbonyl)methyl-1,3-dimethyluracil, a compound that may have potential applications in the development of new drugs and therapeutic agents.
3. To synthesize new highly conjugated propenylidene derivatives via aromatic Paterno-Buchi type cycloaddition with 1-methoxynaphthalene, which could be used in the development of novel pharmaceutical compounds.
Additionally, 5-FDMU has been reported to have antineoplastic properties, making it a potential candidate for further research and development in cancer treatment. Its chemical reactivity allows for various reactions, such as oxidation, photosubstitution, and cycloaddition, which can lead to the development of new compounds with potential pharmaceutical applications.

Synthesis Reference(s)

Tetrahedron, 46, p. 3093, 1990 DOI: 10.1016/S0040-4020(01)88400-3

InChI:InChI=1/C6H7FN2O2/c1-8-3-4(7)5(10)9(2)6(8)11/h3H,1-2H3

Upstream product

• 51-21-8 5-fluorouracil 
• 74-88-4 methyl iodide 

Downstream Products

• 75993-41-8 5-fluoro-2,6-dihydroxynicotinamide 
• 75993-41-8 5-Fluoro-2-hydroxy-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid amide 
• 97961-45-0 1,3-dimethyl-2,5-dioxoimidazolidin-4-yl acetate 
• 97961-46-1 3-Chloro-benzoic acid 1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl ester 
• 92207-40-4 3-Chloro-benzoic acid 1,3-dimethyl-2,5-dioxo-imidazolidin-4-yl ester 
• 83472-56-4 N₁,N₃-dimethyl-5-fluoro-5,6-dihydrouracil 
• 105202-34-4 1,3-dimethyl-5-o-tolylpyrimidine-2,4(1H,3H)-dione 
• 105202-36-6 1,3-dimethyl-5-p-tolylpyrimidine-2,4(1H,3H)-dione 
• 105202-35-5 1,3-dimethyl-5-(m-tolyl)pyrimidine-2,4(1H,3H)-dione 
• 105202-37-7 1,3-dimethyl-6-o-tolylpyrimidine-2,4(1H,3H)-dione 
• 105202-39-9 1,3-dimethyl-6-p-tolylpyrimidine-2,4(1H,3H)-dione 
• 105202-38-8 1,3-dimethyl-6-(3-methylphenyl)uracil 
• 105183-73-1 6-Cyclohex-1-enylmethyl-5-fluoro-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 1070363-57-3 methyl 2-[(1E,3Z)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-prop-1-enyl]benzoate 

Relevant academic research and scientific papers

Photochemical synthesis of benzopyrimidosemibullvalenesfrom benzopyrimidobarrelenes

UV irradiation (λ=254 nm) of 5-fluoro-1,3-dimethyluracil with naphthalene afforded a novel benzopyrimidosemibullvalene derivative with H and F atoms remaining intact on the newly constructed moiety. It was found that the semibullvalene could be derived from the initially produced barrelene derivative during irradiation.

The photocycloaddition reactions of uridine and related compounds with 2,3-dimethyl-2-butene

The photochemical reactions of uracil and 5-fluorouracil derivatives with simple alkenes have been investigated. Photocycloaddition of uracil or 5-fluorouracil derivatives and 2,3-dimethyl-2-butene in acetone gave an enantiomeric mixture of cross cycloadducts (4, 7) in moderate yields. Under similar conditions, diastereomers of 4-substituted 7,7,8,8-tetramethyl-cis-2,4-diazabicyclo[4.2.0]octane-3,5-dione nucleosides (14-17) were formed from uridine or 5-fluorouridine derivatives in good yields. The structures and stereochemistry of these cycloadducts of the nucleoside series were elucidated on the basis of the proton nuclear magnetic resonance spectra and X-ray crystallographic analysis.