4869-46-9

Basic information

• Product Name: 1,3-DIMETHYLURACIL-5-CARBOXALDEHYDE
• Synonyms: 1,3-Dimethyluracil-5-carboxaldehyde;1,3-dimethyl-2,4-dioxo-pyrimidine-5-carbaldehyde;1,3-dimethyl-2,4-dioxopyrimidine-5-carbaldehyde;2,4-diketo-1,3-dimethyl-pyrimidine-5-carbaldehyde;1,3-Dimethyl-5-formyluracil;1,2,3,4-tetrahydro-1,3-diMethyl-2,4-dioxopyriMidine-5-carbaldehyde
• CAS NO: 4869-46-9
• Molecular Formula: C₇H₈N₂O₃
• Molecular Weight: 168.15
• Mol File: 4869-46-9.mol

Chemical Properties

• Boiling Point: 274.1 °C at 760 mmHg
• Flash Point: 122.6 °C
• Appearance: /
• Density: 1.408 g/cm³
• Vapor Pressure: 0.00551mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -3.06±0.40(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 1,3-DIMETHYLURACIL-5-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIMETHYLURACIL-5-CARBOXALDEHYDE(4869-46-9)
• EPA Substance Registry System: 1,3-DIMETHYLURACIL-5-CARBOXALDEHYDE(4869-46-9)

Safety Data

• Hazardous Substances Data: 4869-46-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3-Dimethyluracil-5-carboxaldehyde is used as a building block in organic synthesis for the preparation of various compounds. Its unique structure allows for the formation of new chemical bonds and the creation of diverse molecules with potential applications in different fields.
Used in Pharmaceutical Industry:
1,3-Dimethyluracil-5-carboxaldehyde is used as a key intermediate in the synthesis of pharmaceuticals and other biologically active compounds. Its presence in the molecular structure of these compounds can influence their properties, such as solubility, stability, and biological activity, making it a valuable component in drug development.
Used in Research and Development:
1,3-Dimethyluracil-5-carboxaldehyde is utilized in research and development for studying the properties and potential applications of uracil derivatives. Its reactivity and structural features make it an interesting subject for scientific investigations, which can lead to the discovery of new compounds and applications.

InChI:InChI=1/C7H8N2O3/c1-8-3-5(4-10)6(11)9(2)7(8)12/h3-4H,1-2H3

Upstream product

• 874-14-6 1,3-dimethyluracil 
• 68-12-2 N,N-dimethyl-formamide 
• 4401-71-2 1,3-dimethylthymine 
• 66224-66-6 adenine 
• 74226-50-9 (E)-2-<(1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)methylene>hexanenitrile 
• 74226-51-0 (Z)-2-<(1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)methylene>hexanenitrile 
• 49846-86-8 6-cyano-1,3-dimethyluracil 
• 1195-08-0 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde 
• 74-88-4 methyl iodide 

Downstream Products

• 134924-74-6 5-(Furan-2-yl-hydroxy-methyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 134924-75-7 5-[1-Furan-2-yl-meth-(E)-ylidene]-6-hydroxy-1,3-dimethyl-dihydro-pyrimidine-2,4-dione 
• 874-14-6 1,3-dimethyluracil 
• 96-31-1 N,N'-Dimethylurea 
• 74442-97-0 3-(Ethoxycarbonyl)-4-hydroxy-N-methylbenzamide 
• 80981-29-9 1,3-dimethyluracil-5-carbaldehyde phenylhydrazone 

Relevant articles and documents

Enantioselective Synthesis of D -α-(Uracil-5-yl)glycine Derivatives and Their Racemization-Free Incorporation into a Model Peptide

An efficient asymmetric synthesis of D-α-(uracil-5-yl)glycine derivatives using an enzymatic dynamic kinetic resolution of D,L-hydantoin intermediates with an immobilized D-hydantoinase (D-Hyd-1) is described. In addition, mild conditions for a racemization-free solid-phase peptide synthesis (SPPS) using the Fmoc strategy have been found.

A structure-specific small molecule inhibits a miRNA-200 family member precursor and reverses a type 2 diabetes phenotype

MicroRNA families are ubiquitous in the human transcriptome, yet targeting of individual members is challenging because of sequence homology. Many secondary structures of the precursors to these miRNAs (pri- and pre-miRNAs), however, are quite different. Here, we demonstrate both in vitro and in cellulis that design of structure-specific small molecules can inhibit a particular miRNA family member to modulate a disease pathway. The miR-200 family consists of five miRNAs, miR-200a, -200b, -200c, -141, and -429, and is associated with type 2 diabetes (T2D). We designed a small molecule that potently and selectively targets pre-miR-200c's structure and reverses a pro-apoptotic effect in a pancreatic β cell model. In contrast, an oligonucleotide targeting the RNA's sequence inhibited all family members. Global proteomics and RNA sequencing analyses further demonstrate selectivity for miR-200c. Collectively, these studies establish that miR-200c plays an important role in T2D, and small molecules targeting RNA structure can be an important complement to oligonucleotides.

Synthesis of 5-hetaryluracil derivatives via 1,3-dipolar cycloaddition reaction

1,3-Dipolar cycloaddition is a convenient method for construction of various heterocyclic systems. We applied this method for the synthesis 5-hetaryluracil derivatives where substituted uracils played the role of 1,3-dipoles or dipolarophiles. Treatment of the nitrile oxide derived from 5-formyluracil and substituted alkenes gave the appropriate 5-(4,5-dihydroisoxazol-3-yl)pyrimidine-2,4(1H,3H)-diones, which by oxidation with N-bromosuccinimide were transformed into appropriate 5-(isoxazol-3-yl)uracils. When 5-cyanouracil was used as a dipolarophile in the reaction with nitrile oxides, generated from aromatic aldoximes, several 5-(1,2,4-oxadiazol-5-yl)uracils were obtained. An alternative reaction of 5-formyluracil with an excess of nitriles in the presence of cerium ammonium nitrate as an oxidant gave 1,2,4-oxadiazol-3-yl derivatives in moderate yields. (Chemical Equation Presented).

The arylimines of 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde: Synthesis and their application in 1,3-dipolar cycloaddition reaction

(Chemical Equation Presented) A number of aldimines have been obtained in very good yield in reaction of 5-formyl-1,3-dimethyluracil with various substituted anilines in boiling methanol. Selected aldimines were treated with nitrile oxides generated from 4-chlorobenzaldoxime or 4-methylbenzaldoxime forming the appropriate 1,3-cycloadducts in moderate yields.

Gonadotropin releasing hormone receptor antagonists

The present invention relates to Gonadotropin Releasing Hormone (“GnRH”) (also known as Leutinizing Hormone Releasing Hormone) receptor antagonists.

Stereoselective routes to substituted β-amino carbonyl compounds via heterodiene [4π+2π] cycloadditions of auxiliary-based C2 symmetric ketene acetals

Heterodiene [4π+2π] cycloadditions of (S,S)-4,5-diaryl-2-methylene-1,3-dioxolanes 1 to a series of β-amido-α,β-unsaturated carbonyl compounds are diastereoselective (d.r.≥4:1). The products can be purified by trituration or crystallisation and hydrolysed with acid to generate the corresponding β-amido carbonyl compounds, the overall sequence effecting an auxiliary-based enantioselective conjugate addition of an acetate enolate, leading to β-aminoacid derivatives.

Oxidation of 1,3-dimethylthymine and 1,3-dimethyluracil with oxone in the solid to solid state

The oxidation of the title substrates with Oxone in the presence of camphor in the solid to solid state afforded a simple and efficient method for epoxidation under mild reaction condition.

Oxidation of 1,3-dimethylthymine with oxone catalyzed by 5,10,15,20-tetrakis (4N-methylpyridiniumyl)porphyrinatomanganese (III) pentaacetate

The reaction of 1,3-dimethylthymine 2 with KHSO5 (oxone) catalyzed by 5, 10, 15, 20-tetrakis-(4N-methylpyridiniumyl)porphyrinatomanganese (III) pentaacetate 1 [T4MPyPMn (III) (OAc)5] in phosphate buffer gives 1,3-dimethyl-5-hydroxymethyluracil 3, 1,3-dimethyl-5-formyluracil 4, 1,3-dimethyluracil-5-carboxylic acid 5, cis-1,3-dimethylthymine-5,6-glycol 6 and 1,3,5-trimethyl-5-hydroxybarbituric acid 8 in different yields depending on the pH of the reaction medium. Oxidation of the 5-methyl group of 1,3-dimethylthymine to 1,3-dimethyl-5-hydroxymethyluracil 3, 1,3-dimethyl-5-formyluracil 4 and the corresponding acid 5 with oxone catalyzed by T4MPyPMn (III) (OAc)5 may be explained by hydrogen abstraction and recombination mechanism, whereas oxidation of 5,6-double bond of thymine to cis-1,3-dimethylthymine-5,6-glycol 6 and 1,3,5-trimethyl-5-hydroxybarbituric acid 8 may be explained either by electron transfer followed by oxygen atom transfer or by the involvement of hydroxy radicals.

Oxidation of nucleic acid related compounds by the peroxodisulfate ion

The treatment of nucleic acid bases, nucleosides, and nucleotides with peroxodisulfate ion in a phosphate buffer solution at pH 7.0 or water at 70-75°C was investigated. The reaction of thymine and 5-methylcytosine nucleosides and nucleotides resulted in the oxidation of the 5-methyl groups. The oxidation products from 1,3-dimethyluracils and the time-course of the reaction of uracils led to two plausible reaction mechanisms for the oxidation of uracils.