3055-23-0

Basic information

• Product Name: (2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde
• Synonyms: (2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde; 1(2H)-pyrimidineacetaldehyde, 3,4-dihydro-2,4-dioxo-
• CAS NO: 3055-23-0
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.1234
• Mol File: 3055-23-0.mol
• Article Data: 4

Chemical Properties

• Density: 1.343g/cm³
• Refractive Index: 1.517
• CAS DataBase Reference: (2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde(3055-23-0)
• EPA Substance Registry System: (2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde(3055-23-0)

Safety Data

• Hazardous Substances Data: 3055-23-0(Hazardous Substances Data)

Usage

Description

(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde is a chemical compound with the molecular formula C6H6N2O3. It is a derivative of the pyrimidine ring and contains a reactive aldehyde group. (2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde is often used as an intermediate in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. It can undergo various chemical reactions to form complex molecules with diverse medicinal and agricultural applications. (2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde is important in the field of medicinal chemistry and drug discovery due to its versatile reactivity and ability to be modified into a wide range of bioactive compounds. Its unique structure and functional groups make it a valuable building block in the synthesis of new chemical entities with potential therapeutic properties.

Uses

Used in Pharmaceutical Industry:
(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde is used as an intermediate in the synthesis of various pharmaceuticals for its versatile reactivity and ability to be modified into a wide range of bioactive compounds.
Used in Agrochemical Industry:
(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde is used as an intermediate in the production of agrochemicals for its potential to form complex molecules with diverse agricultural applications.
Used in Medicinal Chemistry and Drug Discovery:
(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetaldehyde is used as a building block in the synthesis of new chemical entities with potential therapeutic properties due to its unique structure and functional groups.

Upstream product

• 3054-58-8 1-(2,2-Diaethoxy-aethyl)-uracil 
• 66-22-8 uracil 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 

Downstream Products

• 175228-79-2 (S)-2-[2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-methylcarbamoyl-ethylamino]-3-methyl-butyric acid methyl ester 
• 134834-61-0 β-(1-Uracilyl)-α-benzylaminopropionitrile 
• 134834-63-2 β-(1-Uracilyl)-α-benzylaminopropionamide 
• 134834-66-5 β-(5-Benzylamino-1-uracilyl)-α-hydroxypropioc acid benzylamide 

Relevant articles and documents

A Chemoenzymatic Route to Prepare Acyclic Nucleoside Analogues

Acyclic nucleosides are potential antiviral and antitumor agents. In this work, their preparation through a novel chemoenzymatic procedure involving the N-alkylation of a nucleobase and subsequent aldol condensation catalyzed by a dihydroxyacetone phosphate-dependant aldolase (Rabbit Muscle Aldolase, RAMA) is described.

A short de novo synthesis of nucleoside analogs

Nucleoside analogs are commonly used in the treatment of cancer and viral infections. Their syntheses benefit from decades of research but are often protracted, unamenable to diversification, and reliant on a limited pool of chiral carbohydrate starting materials. We present a process for rapidly constructing nucleoside analogs from simple achiral materials. Using only proline catalysis, heteroaryl-substituted acetaldehydes are fluorinated and then directly engaged in enantioselective aldol reactions in a one-pot reaction. A subsequent intramolecular fluoride displacement reaction provides a functionalized nucleoside analog. The versatility of this process is highlighted in multigram syntheses of D- or L-nucleoside analogs, locked nucleic acids, iminonucleosides, and C2′- and C4′-modified nucleoside analogs. This de novo synthesis creates opportunities for the preparation of diversity libraries and will support efforts in both drug discovery and development.

Synthesis of novel mimetics of CMP-sialic acid as the inhibitors of sialyltransferases

Novel mimetics of CMP-sialic acid were designed as the inhibitors of sialyltransferases. They were synthesized in a short step from a cytosine carrying β-hydroxy-α-L-amino acid based on the knowledge that nikkomycin, a peptidic derivative of an uracil carrying amino acid, shows a potent inhibitory activity toward N-acetyl-D-glucosaminyltransferases that employ UDP-N-acetyl-D-glucosamine as the donor substrate. The cytosine carrying β-hydroxyl-α-L-amino acid, a key intermediate in our synthetic strategy, was easily prepared by the L-threonine aldolase (LTA) catalyzed reaction.