53369-66-7

Upstream product

• 64-10-8 phenyl carbamate 
• 51-20-7 5-bromouracil 
• 108-90-7 chlorobenzene 
• 15533-68-3 1-phenyldihydropyrimidine-2,4(1H,3H)-dione 
• 21321-07-3 1-phenyluracil 

Downstream Products

• 1357351-13-3 3-(3-ethyl-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydropyrimidin-5-yl)benzoic acid ethyl ester 
• 1357349-99-5 5-(3-chlorophenyl)-3-ethyl-1-phenyl-1H-pyrimidine-2,4-dione 
• 1358965-66-8 3-ethyl-5-(3-nitrophenyl)-1-phenyl-1H-pyrimidine-2,4-dione 
• 1357350-56-1 5-bromo-3-cyclopropylmethyl-1-phenyl-1H-pyrimidine-2,4-dione 
• 1357350-08-3 5-bromo-3-ethyl-1-phenyl-1H-pyrimidine-2,4-dione 
• 352017-39-1 5-amino-1-phenylpyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Solid-supported synthesis of N-alkylated derivatives of 5-bromo pyrimidine-2, 4-dione and Study of their cytotoxic effect

The presented study reports the synthesis of 5-bromo substituted pyrimidine-2,4-dione by conventional and solid-state microwave-assisted methodology. 5-bromo pyrimidine-2,4-dione derivatives represent the novel group of compounds possessing remarkable anti-tumor and antibacterial activities with significant therapeutic effects such as anti-neoplastic as well. Thus, a diversity-oriented convergent synthesis of complex organic molecules from simple and readily available substrates has been carried out that has resulted in the derivatization of 5-bromo pyrimidine-2,4 dione predominately giving N1 and N3 substituted compounds where R may be the alkyl, aryl, cyclohexyl methyl etc. In addition, use of solid-state microwave-assisted protocol proved to be of vital importance in terms of energy efficiency and designing a solvent-free ecofriendly synthetic route with considerably reduced reaction time.

Aza analogues of thalidomidesynthesis and evaluation as inhibitors of tumor necrosisfactor-α production in vitro

A synthetic entry to derivatives of the new classes of 5-phthalimidouracils and 5-phthalimidobarbituric acids is reported. These 5-phthalimidopyramines as well as phthalimido-2,4-difluorobenzenes were designed as analogues of thalidomide, a well known inhibitor of TNF-α production. A preliminary in vitro investigation of the compounds as inhibitors of the TNF-α production was performed. Among the compounds of the present series, (5-ethyl-1-phenyl-5- tetrafluorophthalimido)barbituric acid and (2- 2,4-difluorophenyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3 2H)-dione were proved to be potent inhibitors. Both compounds showed inhibitory activity in the lower micromolar range of the LPS-induced TNF-α production in human monocytes. Copyright

Selective Oxidative Halogenation of Uracils

A variety of N-substituted uracils has been selectively brominated to the corresponding 5-bromouracils in high yield by CHBr3-O2.Both oxidative bromination and chlorination of N-substituted uracils can be performed by means of combination of haloalkane solvents with m-chloroperbenzoic acid, magnesium monoperoxyphthalate, tert-butyl hydroperoxide or iodosylbenzene.Intermediates along the reaction path leading to the 5-halouracils have been identified; the intermediates depend on the oxidant used.Mechanistic aspects of the halogenation reactions and the reactive intermediates are discussed.

Photochemistry of Uracils in Halogenated Solvents

The photochemistry of uracil and 1-substituted and 1,3-disubstituted uracils in CHBr3-CH2Cl2 is investigated.Photolysis of uracil leads to the formation of 5,6-dibromo-5,6-dihydrouracil as the main product, with 5-bromouracil as the by-product.In contrast with this the 5-bromouracils are formed as the main products by the photolysis of 1-substituted and 1,3-disubstituted uracils, with the corresponding 5,6-dihydro- and 5-bromo-5,6-dihydrouracils as the by-products.The kinetics of the bromination reaction have also been investigated and based on these results a free radical mechanism is proposed.