49738-24-1

Basic information

• Product Name: 5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE
• Synonyms: 5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE;5-amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• CAS NO: 49738-24-1
• Molecular Formula: C₆H₉N₃O₂
• Molecular Weight: 155.15
• Mol File: 49738-24-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 243.1°Cat760mmHg
• Flash Point: 100.8°C
• Appearance: /
• Density: 1.288g/cm³
• Vapor Pressure: 0.0328mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE(49738-24-1)
• EPA Substance Registry System: 5-AMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE(49738-24-1)

Safety Data

• Hazardous Substances Data: 49738-24-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H9N3O2/c1-8-3-4(7)5(10)9(2)6(8)11/h3H,7H2,1-2H3

Upstream product

• 483-57-8 fervenulin 
• 109-89-7 diethylamine 
• 874-14-6 1,3-dimethyluracil 
• 41613-26-7 1,3-dimethyl-5-nitrouracil 

Downstream Products

• 16952-91-3 5-Acetamido-1,3-dimethyl-uracil 

Relevant articles and documents

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Effect of the 6-methyl group on peroxyl radical trapping by 5-hydroxyand 5-amino-derivatives of 1,3-dimethyluracil

Background: Many synthetic and natural uracil derivatives have biological activity. Furthermore, many of these derivatives have pro- and antioxidant properties, but the mechanism of these processes is far from being understood. Methods: Oxygen-uptake kinetics and computational methods (CBS-QB3, M062X/MG3S and SMDM05/MG3S) were combined to study the reaction of peroxyl radicals with five organic-soluble derivatives: 5-amino- and 5-hydroxy-1,3-dimethyluracil, 5-amino- and 5-hydroxy-1,3,6-trimethyluracil, and 5-hydroxy-1,3-dimethyl-6-phenyluracil in chlorobenzene. Results: The studied uracil derivatives should be classified as inhibitors of medium reactivity kin= (1-10) × 10-4M-1s-1. The methyl group in the 6-position of the pyrimidine ring increases the rate constant of the reaction with peroxyl radicals by 3-4 times and the stoichiometric coefficient of inhibition. The calculation of the reaction barrier heights at the SMD-M05/MG3S level of theory for the hydrogen abstraction is in good agreement with experimental data. Conclusion: 1,3-Dimethyl-5-aminouracil is transformed by the addition of a methyl group at the 6-position into a favic-like pyrimidine, while the 5-hydroxy derivative becomes a more effective antioxidant. The bound dissociation energy (O-H or N-H) and the IP for the reactivity forecasting of uracil derivatives were used, but it was found that this methodology did not lead to good correlation between experimental and theoretical results. The SMD-M05/MG3S method provided the most accurate calculations of the reaction barrier heights for hydrogen abstraction from uracil derivatives by peroxyl radical.

Indirect C-H azidation of heterocycles via copper-catalyzed regioselective fragmentation of unsymmetrical λ3-iodanes

A C-H bond of electron-rich heterocycles is transformed into a C-N bond in a reaction sequence comprising the formation of heteroaryl(phenyl)iodonium azides and their in situ regioselective fragmentation to heteroaryl azides. A Cu(I) catalyst ensures complete regiocontrol in the fragmentation step and catalyzes the subsequent 1,3-dipolar cycloaddition of the formed azido heterocycles with acetylenes. The heteroaryl azides can also be conveniently reduced to heteroarylamines by aqueous ammonium sulfide. The overall C-H to C-N transformation is a mild and operationally simple one-pot sequential multistep process.