156398-76-4

Basic information

• Product Name: 1,3-dimethyl-2,4-pyrimidinione
• Synonyms: 1,3-dimethyl-2,4-pyrimidinione
• CAS NO: 156398-76-4
• Molecular Formula: C6H8N2O2
• Molecular Weight: 140.14
• Mol File: 156398-76-4.mol
• Article Data: 74

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-dimethyl-2,4-pyrimidinione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dimethyl-2,4-pyrimidinione(156398-76-4)
• EPA Substance Registry System: 1,3-dimethyl-2,4-pyrimidinione(156398-76-4)

Safety Data

• Hazardous Substances Data: 156398-76-4(Hazardous Substances Data)

Upstream product

• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 66-22-8 uracil 
• 77-78-1 dimethyl sulfate 
• 49785-67-3 1,3-dimethyl-4-thiouracil 
• 103408-62-4 1,3-dimethyl-6-tributylstannyluracil 
• 4869-46-9 1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 
• 4116-38-5 1,3-dimethylorotic acid 
• 118237-90-4 2,4,7,7,8,8-hexamethyl-cis-2,4-diazabicyclo<4.2.0>octane-3,5-dione 
• 31356-07-7 trans,anti-(1,3-dimethyluracil) dimer 
• 85199-75-3 1,3-dimethyl-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione 
• 624-31-7 4-tolyl iodide 
• 1204139-34-3 2,2-dimethyl-5-(N-methyl-N-methylcarbamoylaminomethylene)-1,3-dioxane-4,6-dione 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 769-42-6 1,3-dimethylbarbituric acid 

Downstream Products

• 104139-64-2 5-(1-Benzyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 84174-99-2 4-[3-Chloro-4-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-yl]-benzoic acid ethyl ester 
• 124851-78-1 5-cyclohexyl-1,3-dimethyluracil 
• 32079-08-6 5-Acetoxymethyl-1,3-dimethyluracil 
• 129056-81-1 5-Carboxymethyl-1,3-dimethyluracil 
• 10211-36-6 3-phenyl-pyridine-2,6-diol 
• 10211-36-6 6-Hydroxy-5-phenyl-1H-pyridin-2-one 
• 1224944-43-7 sodium pyrazolo[1,5-a] pyrimidin-5-olate 
• 1613623-85-0 5-(3-fluorophenyl)-1,3-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione 
• 1613623-72-5 {2-[5-(3-chlorophenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrrolo[3,4-d]pyrimidin-6-yl]ethyl}carbamic acid tert-butyl ester 
• 1613622-52-8 (8R,10R)-10-(5-chlorofuran-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-7,8-dihydro-1H-pyrimido[4',5:3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione 
• 1613622-56-2 (8R)-10-(5-chlorofuran-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-7,8-dihydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione 

Relevant articles and documents

A Possible Chain Reaction in Photosensitized Splitting of Pyrimidine Dimers by a Protonated, Oxidized Flavin

Pyrimidine dimer cycloreversion was photosensitized by protonated 2',3',4',5'-tetraacetylriboflavin (ac4rfH+), whereas the protonated flavin radical (ac4rfH2.+) failed to sensitize detectable dimer splitting.In acetonitrile containing 0.075percent perchloric acid, the ac4rf absorption bands at 375 nm and 445 nm are replaced by a new band at 390 nm due to ac4rfH+.Irradiation of ac4rfH+ in the presence of cis,syn- or trans,syn-1,3-dimethyluracil dimer resulted in efficient cycloreversion to 1,3-dimethyluracil, probably induced by electron abstraction from the dimer by ac4rfH+ to produce the dimer radical cation.The quantum yields of splitting were large (Φspl = 0.35 and 1.5 for cis,syn and trans,syn isomers, respectively, at = 1.2 mM).Splitting quantum yields increased with dimer concentration in a quadratic fashion.These results are consistent with the occurance of a chain reaction propagated by monomer.+ + dimer -> monomer + dimer.+ in the case of the dimethyluracil dimers.The fluorescence of the protonated flavin (λem = 507 nm) was found to be quenched by the dimers.In the presence of small amounts of added water, however, both the fluorescence quenching and splitting were abolished.Two cis,syn dimers in which the N(1)- and N(1')-atoms were tethered via a trimethylene bridge exhibited quantum yields of approximately 0.02 at the above dimer concentration.A compound in which ac4rf is covalently bound to a pyrimidine dimer was also found to undergo splitting in acidified acetonitrile (Φ = 0.03).These values are more than 1 order of magnitude greater than those reported for unprotonated flavins.

Photochemical behaviour of 5-perfluoroalkenyl uracils

Phototransformations of derivatives of 5-fluoroalkenyl uracils depend strongly on the fluorinated substituents. 1,3-Dimethyl-5-trifluorovinyluracil when irradiated in water with UV light (λ>300nm) gives 1,3-dimethyl-(5,6-dihydrourac-6-yl)-difluoroacetic a

Letter: Mechanism of decarboxylation of 1,3-dimethylorotic acid. A possible role for orotate decarboxylase.

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A multi-step photoreaction of 5-formyl-1,3-dimethyluracil with indole in the solid state

Irradiation of the mixed crystals between 5-formyl-1,3-dimethyluracil (1) and indole (2) gave 5-(bis-1-indolyl)methyl-1,3-dimethyluracil (3), whereas 1,3-dimethyluracil was the sole product in the photolysis of 1 and 2 in solution.

Carbanions from decarboxylation of orotate analogs: Stability and mechanistic implications

The pKa's of the 6-CH groups of 1,3-dimethyluracil, N-methyl-2-pyridone, and N-methyl-4-pyridone were determined through their reactions with bases derived from carbon acids with known pKa and the reactions of their corresponding carbanions with the carbon acids. No correlation between the stability of the carbanions and the rate of decarboxylation of corresponding carboxylic acids was found.

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Fenton chemistry of 1,3-dimethyluracil

Hydroxyl radicals were generated in the Fenton reaction at pH 4 (Fe2+ + H2O2 → Fe3+ + ?OH + OH-, k ≈ 60 L mol-1 s-1) and by pulse radiolysis (for the determination of kinetic data). They react rapidly with 1,3-dimethyluracil, 1,3-DMU (k = 6 × 109 L mol-1 s-1). With H2O2 in excess and in the absence of O2, 1,3-DMU consumption is 3.3 mol per mol Fe2+. 1,3-DMUglycol is the major product (2.95 mol per mol Fe2+). Dimers, prominent products of ?OH-induced reactions in the absence of Fe2+/Fe3+ (Al-Sheikhly, M.; von Sonntag, C. Z. Naturforsch. 1983, 31b, 1622) are not formed. Addition of ?OH the C(5)-C(6) double bond of 1,3-DMU yields reducing C(6)-yl 1 and oxidizing C(5)-yl radicals 2 in a 4:1 ratio. The yield of reducing radicals was determined with tetranitromethane by following the buildup of nitroform anion. Reaction of 1 with Fe3+ that builds up during the reaction or with H2O2 gives rise to a short-chain reaction that is terminated by the reaction of Fe2+ with 2, which re-forms 1,3-DMU. In the presence of O2, 1.1 mol of 1,3-DMU and 0.6 mol of O2 are consumed per mol Fe2+ while 0.16 mol of 1,3-DMU-glycol and 0.17 mol of organic hydroperoxides (besides further unidentified products) are formed. In the presence of O2, 1 and 2 are rapidly converted into the corresponding peroxyl radicals (k = 9.1 × 108 L mol-1 s-1). Their bimolecular decay (2k = 1.1 × 109 L mol-1 s-1) yields ～22% HO2?/O2?- in the course of fragmentation reactions involving the C(5)-C(6) bond. Reduction of Fe3+ by O2?- leads to an increase in ?OH production that is partially offset by a consumption of Fe2+ in its reaction with the peroxyl radicals (formation of organic hydroperoxides, k ≈ 3 × 105 L mol-1 s-1; value derived by computer simulation).

Synthesis of some 5-perfluoroalkenyl derivatives of uracil

1,3-Dimethyl-5-iodouracil reacts smoothly with perfluorovinyl- (and E/Z-pentafluoropropenyl)-zinc iodides in the presence of Pd0 as a catalyst yielding the appropriate 5-perfluoroalkenyl derivatives of uracil at high and moderate yield.In an analogous reaction, 1,3-dimethyl-6-iodouracils did not yield the expected coupling products. - Keywords: Synthesis; Perfluoroalkenyl uracils; NMR spectroscopy; Coupling products; Palladium catalyst

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Accelerated decarboxylation of 1,3-dimethylorotic acid in ionic liquid

The solvent effect of ionic liquids on the decarboxylation of 1,3-dimethylorotic acid and its analogue in ionic was investigated. The rate acceleration observed was proposed to be a result of the stabilization of the zwitterionic intermediates by the charged groups available in these special solvents.

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Copper-Catalyzed Regioselective Direct C–H Thiolation and Thiocyanation of Uracils

A novel copper-catalyzed direct C–H thiolation and thiocyanation of uracils using disulfides and thiocyanate salts respectively as coupling partners are described. These reactions enable the C–H bond cleavage and C–S bond formation to proceed efficiently under relatively mild conditions, providing useful methods for a preparation of a series of thio-substituted at the C5 position of uracil derivatives. These protocols exhibit several merits including simple experimental procedures, readily accessible substrates and reagents, broad scopes, high yields, and excellent regioselectivity. Preliminary mechanistic studies revealed that a radical pathway is likely to be involved.

Photocatalytic Systems with Flavinium Salts: From Photolyase Models to Synthetic Tool for Cyclobutane Ring Opening

Two new photocatalytic systems based on flavinium species formed in situ by protonation of riboflavin-tetraacetate (1) with triflic acid or prepared in advance via alloxazine quaternization are presented as effective tools for oxidative cyclobutane ring [2 + 2] cycloreversion using visible light. The system with 1,3-dimethyl-8-trifluoromethylalloxazinium perchlorate (2c) was found to be superior allowing an acid-free mild procedure, which results in the opening of cyclobutanes with high oxidation potential (up to 2.14 V) and/or with sensitive groups (e.g., furan) without side reactions.