13509-52-9

Basic information

• Product Name: 1,3,4-TRIMETHYL URACIL
• Synonyms: 1,3,4-TRIMETHYL URACIL;1,3,6-TRIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE;1,3,6-trimethyluracil;1,3,6-Trimethyl-2,4(1H,3H)-pyrimidinedione;1,3,6-Trimethyl-1H,3H-pyrimidine-2,4-dione;1,3,6-Trimethyl uracil, >=95%
• CAS NO: 13509-52-9
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 154.17
• EINECS: 236-838-0
• Mol File: 13509-52-9.mol

Chemical Properties

• Melting Point: 114-115℃
• Boiling Point: 222.1±23.0℃ (760 Torr)
• Flash Point: 87.8±15.0℃
• Appearance: /
• Density: 1.160±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.104mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 1,3,4-TRIMETHYL URACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4-TRIMETHYL URACIL(13509-52-9)
• EPA Substance Registry System: 1,3,4-TRIMETHYL URACIL(13509-52-9)

Safety Data

• Hazardous Substances Data: 13509-52-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
1,3,4-Trimethyluracil is used as a neuroprotective agent for its potential to protect the nervous system and improve cognitive function, which is beneficial in conditions affecting the brain and cognitive abilities.
Used in Wound Healing Applications:
1,3,4-Trimethyluracil is used as a promoter of wound healing due to its capacity to enhance the healing process, making it valuable in medical treatments involving skin injuries or surgical recovery.
Used in Anti-Inflammatory Treatments:
1,3,4-Trimethyluracil is used as an anti-inflammatory agent to reduce inflammation, which is crucial in managing conditions characterized by excessive immune responses.
Used in Medical Conditions Treatment:
1,3,4-Trimethyluracil is used as a therapeutic agent for the treatment of various medical conditions, including ischemic stroke, diabetic neuropathy, and traumatic brain injury, due to its potential to mitigate the effects of these conditions and promote recovery.
The applications of 1,3,4-Trimethyluracil (TMU) are diverse, reflecting its multifaceted potential in the medical and pharmaceutical fields. Its ongoing research and development underscore its importance in addressing a range of health issues.

InChI:InChI=1/C7H10N2O2/c1-5-4-6(10)9(3)7(11)8(5)2/h4H,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 626-48-2 6-Methyluracil 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 10128-60-6 3,6-dimethyl-2H-1,3-oxazine-2,4(3H)-dione 
• 7781-23-9 2,4-dimethoxy-6-methylpyrimidine 
• 6220-44-6 4-methoxy-1,6-dimethyl-1H-pyrimidin-2-one 
• 19674-60-3 3,6-dimethyluracil 
• 109-80-8 1.3-propanedithiol 
• 15018-59-4 5-bromo-1,3,6-trimethylpyrimidine-2,4(1 H,3H)-dione 
• 96-31-1 N,N'-Dimethylurea 
• 108-24-7 acetic anhydride 
• 116705-39-6 6-(2-dimethylaminovinyl)-1,3-dimethyluracil 
• 33227-65-5 1,3,6-trimethyl-1H-pyrimidine-2,4-dithione 

Downstream Products

• 100870-67-5 1,3-dimethyl-6-phenacyl-1H-pyrimidine-2,4-dione 
• 15018-59-4 5-bromo-1,3,6-trimethylpyrimidine-2,4(1 H,3H)-dione 
• 55326-07-3 1,3,6-trimethyl-5-nitrouracil 
• 84174-94-7 5-(4-Bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1,3,6-trimethyl-1H-pyrimidine-2,4-dione 
• 84174-92-5 (4aS,4bS,7aR,7bS)-4b,7a-Dibromo-1,3,6,7b-tetramethyl-tetrahydro-pyrrolo[3',4':3,4]cyclobuta[1,2-d]pyrimidine-2,4,5,7-tetraone 
• 144104-79-0 1,3-dimethyl-5-(2,6-dichlorobenzoyl)-6-methyluracil oxime 
• 144104-80-3 3-(2,6-dichlorophenyl)-5,7,8-trimethyl-8,9-dihydroisoxazolo<5,4-d>pyrimidine-4,6(5H,7H)-dione 
• 144459-80-3 5-cyclohexyl-1,3,6-trimethyluracil 
• 144459-81-4 6-cyclohexylmethyl-1,3-dimethyluracil 
• 144785-53-5 1,3-Dimethyl-7-methylsulfanyl-5-phenyl-1H-quinazoline-2,4-dione 
• 144785-52-4 1-phenyl-1-hydroxy-2-(1,3-dimethyluracil-6-yl)ethane 
• 84174-98-1 5-[4-Chloro-1-(3,5-dichloro-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1,3,6-trimethyl-1H-pyrimidine-2,4-dione 
• 109178-92-9 5-Acetoxymethyl-1,3,6-trimethyl-2,4(1H,3H)-pyrimidinedione 
• 129056-82-2 (1,3,6-Trimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetic acid 

Relevant articles and documents

Photoinduced electron transfer to pyrimidines and 5,6-dihydropyrimidine derivatives: Reduction potentials determined by fluorescence quenching kinetics

The dynamics of flourescence quenching of excited state electron donor sensitizers by various pyrimidine and 5,6-dihydropyrimidine substrates was examined. For all of the substrates studied the rate constant of fluorescence quenching (kq) increases as the excited state oxidation potential (Eox*) becomes more negative. The dependence of kq on Eox* in each case is well described by the Rehm-Weller relationship. Fits of the data to this relationship allow for the estimation of the reduction potentials of the substrates (Ered). The pyrimidines 1,3-dimethylthymine, 1,3-dimethyluracil, and 1,3,6-trimethyluracil give Ered values (in CH3CN) ranging from -2.06 (vs SCE) to -2.14 V. Their dihydro derivatives, 1,3-dimethyl-5,6-dihydrothymine, 1,3-dimethyl-5,6-dihydrouracil, and 1,3,6-trimethyl-5,6-dihydrouracil gave Ered values ranging from -1.90 to -2.07 V. The higher Ered values for the dihydropyrimidines compared with their unsaturated derivatives is attributed to aromatic stabilization in the pyrimidines, which is not present in the dihydro derivatives. In addition, the Ered for both the trans-syn and cis-syn diastereomers of the dimethylthymine cyclobutane dimer was examined using the same method. The trans-syn dimer gives an Ered of -1.73 V and the cis-syn dimer gives an Ered of -2.20 V. This remarkable difference is attributed to a stereoelectronic effect. The cis-syn dimer anion radical suffers from an unfavorable charge-dipole interaction between the added electron and the O4 carbonyl group in the remaining pyrimidine ring. In contrast, the trans-syn dimer anion radical shows mainly a stabilizing inductive electron-withdrawing effect of the remaining O4 carbonyl group. Solvent effects on Ered were also examined. It is shown that the protic solvent, CH3OH, significantly stabilizes the anion radicals, raising Ered by ca. 400 mV over the value in CH3CN.

Antiparasitic activity of highly conjugated pyrimidine-2,4-dione derivatives

4-[2-(1,3-Dimethyl-5-nitro-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl) vinyl]benzaldehyde was synthesized in four steps from 6-methyl-1H,3H-pyrimidine- 2,4-dione. This aldehyde was functionalized by various substituted anilines or substituted benzylamines. Antiparasitic activities of the corresponding azomethines were assessed against Plasmodium falciparum, Trichomonas vaginalis and Leishmania infantum compared to their toxicity versus human cells.

Unlocking Access to Enantiopure Fused Uracils by Chemodivergent [4+2] Cross-Cycloadditions: DFT-Supported Homo-Synergistic Organocatalytic Approach

The discovery of chemical methods enabling the construction of carbocycle-fused uracils which embody a three-dimensional and functional-group-rich architecture is a useful tool in medicinal chemistry oriented synthesis. In this work, an unprecedented amine-catalyzed [4+2] cross-cycloaddition is documented; it involves remotely enolizable 6-methyluracil-5-carbaldehydes and β-aryl enals, and chemoselectively produces two novel bicyclic and tricyclic fused uracil chemotypes in good yields with a maximum level of enantiocontrol. In-depth mechanistic investigations and control experiments support an intriguing homo-synergistic organocatalytic approach, where the same amine organocatalyst concomitantly engages both aldehyde partners in a stepwise eliminative [4+2] cycloaddition, whose vinylogous iminium ion intermediate product may diverge—depending upon conditions—to either bicyclic targets by hydrolysis or tricyclic products by a second homo-synergistic trienamine-mediated stepwise [4+2] cycloaddition.

A potent and selective inhibition of parainfluenza 1 (Sendai) virus by new 6-oxiranyl-, 6-methyloxiranyluracils, and 4(3H)-pyrimidinone derivatives

Several new 6-oxiranyl-, 6-methyloxiranyluracils, and pyrimidinone derivatives, synthesized by the lithiation-alkylation sequence of 1,3,6- trimethyluracil, 1,3-dimethyl-6-chloromethyluracil, and 2-alkoxy-6-methyl- 4(3H)-pyrimidinones, showed a potent and selective antiviral activity against the parainfluenza 1 (Sendai) virus replication.

Effect of a cobalt(II) complex on the radical reaction of vinyl type sulfides. A 'radico-catalysis'

Vinyl type sulfides show increased radicophilicity at the β-position via the coordination to a cobalt(II) complex, and hence the balance between Smiles rearrangement and an ortho-substitution, in vinyl type sulfides having an intramolecular alkyl radical, is lost to favor the latter reaction.

Skeletally Diverse Synthesis of Innovative [2,1-c]-1,4-Oxazepine and [1,4]-Quinoxaline Systems

An efficient, innovative synthesis of [2,1-c]-1, 4-oxazepine and [1,4]-quinoxaline heterocycles along with the embodied pyrimido-pyrrolo motifs was established. Initially, the pyrrole ring was installed using microwave irradiation through an intramolecular base-catalyzed cyclization between acetyl bromomethyl pyrimidine dione and o-amino phenyl methanol or o-phenylenediamine methyl benzoates. Furthermore, oxazepine, and quinoxaline scaffolds were constructed by an acid-catalyzed condensation with a variety of aldehydes by an unconventional Pictet-Spengler reaction strategy. An important aspect of this work is to build novel heterocyclic ring systems with potential medicinal interest.

Highly Efficient Synthesis of Substituted 3,4-Dihydropyrimidin-2-(1H)-ones (DHPMs) Catalyzed by Hf(OTf)4: Mechanistic insights into reaction pathways under metal Lewis acid catalysis and solvent-free conditions

In our studies on the catalytic activity of Group IVB transition metal Lewis acids, Hf(OTf)4 was identified as a highly potent catalyst for”one-pot, three-component” Biginelli reaction. More importantly, it was found that solvent-free conditions, in contrast to solvent-based conditions, could dramatically promote the Hf(OTf)4-catalyzed formation of 3,4-dihydro-pyrimidin-2-(1H)-ones. To provide a mechanistic explanation, we closely examined the catalytic effects of Hf(OTf)4 on all three potential reaction pathways in both “sequential bimolecular condensations” and “one-pot, three-component” manners. The experimental results showed that the synergistic effects of solvent-free conditions and Hf(OTf)4 catalysis not only drastically accelerate Biginelli reaction by enhancing the imine route and activating the enamine route but also avoid the formation of Knoevenagel adduct, which may lead to an undesired byproduct. In addition, 1H-MMR tracing of the H-D exchange reaction of methyl acetoacetate in MeOH-d4 indicated that Hf(IV) cation may significantly accelerate ketone-enol tautomerization and activate the β-ketone moiety, thereby contributing to the overall reaction rate.

Reaction of Halogenated Uracils with KI

Treatment of 5-iodo-1,3,6-trimethyluracil or 5-bromo-1,3,6-trimethyluracil with H2SO4 (5%) in the presence of an excess of KI at 80°C for 5 h produced 1,3,6-trimethyluracil as the only product. Analogous treatment of N-bromo-6-iodomethyluracil gave a mixture with 5-bromo-6-iodomethyluracil as the main constituent. The reaction with an excess of KI in MeOH at 50°C formed 5-bromo-6-hydroxymethyluracil, N(1)-iodo-5-bromo-6-hydroxymethyluracil, N(3)-iodo-5-bromo-6-iodomethyluracil, and 5-bromo-6-iodomethyluracil depending on the reaction time.

Intermediates for macrocyclic compounds

The present invention is directed to novel macrocyclic compounds of formula (I) and their pharmaceutically acceptable salts, hydrates or solvates: wherein R1, R2, R3, R4, R5, R6, n1, m, p Z1, Z2, and Z3 are as describe in the specification. The invention also relates to compounds of formula (I) which are antagonists of the motilin receptor and are useful in the treatment of disorders associated with this receptor and with or with motility dysfunction.

TRICYCLIC COMPOUNDS

The present invention provides a compound of formula I or a pharmaceutically acceptable salt thereof; and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.