76821-79-9

Basic information

• Product Name: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2,4-dioxo-, radical ion(1+) (9CI)
• Synonyms: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2,4-dioxo-, radical ion(1+) (9CI)
• CAS NO: 76821-79-9
• Molecular Formula: C5H4N2O4
• Molecular Weight: 156.09626
• Product Categories: PYRIMIDINE
• Mol File: 76821-79-9.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2,4-dioxo-, radical ion(1+) (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2,4-dioxo-, radical ion(1+) (9CI)(76821-79-9)
• EPA Substance Registry System: 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2,4-dioxo-, radical ion(1+) (9CI)(76821-79-9)

Safety Data

• Hazardous Substances Data: 76821-79-9(Hazardous Substances Data)

Upstream product

• 65-71-4 thymin 
• 4433-40-3 5-hydroxymethyl uracil 
• 1187-34-4 α-Cyano-β-ethoxy-N-(ethoxycarbonyl)acrylamide 
• 65696-20-0 methyl ureidomethylenemalonate 
• 1195-08-0 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde 
• 3650-93-9 5-carboxylcytosine 
• 4425-56-3 5-cyanouracil 
• 110821-07-3 2,4-dimethoxypyrimidine-5-carboxylic acid 

Downstream Products

• 92264-75-0 2,4-dioxohexahydropyrimidine-5-carboxylic acid 
• 1309352-76-8 [Ph(Hiso)(H2O)](n) 
• 3346-68-7 uracil-5-formyl chloride 
• 69312-43-2 2,4-dichloropyrimidine-5-carboxylic acid isopropyl ester 
• 88468-97-7 methyl 1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyridine-5-carboxylate 

Relevant articles and documents

Preparation method of important intermediate (uracil-5-carboxylic acid) of medicine (avanafil)

The invention discloses a preparation method of an important intermediate (uraciluracil-5-carboxylic acid) of a medicine (avanafil), and belongs to the technical field of drug synthesis. The preparation method is characterized in that the uraciluracil-5-carboxylic acid is prepared by adopting thymine as a starting material and using oxygen for further oxidation under the action of an active-carbon-loaded catalyst. The preparation method disclosed by the invention has the advantages of high yield, low cost, economic and environment-friendly effects and applicability to industrialization and thelike and is a synthesis method with industrial production value.

The detrimental effect of orotic acid substitution in the peptide nucleic acid strand on the stability of PNA2:NA triple helices

We have investigated the incorporation of C6 derivatives of uracil into polypyrimidine peptide nucleic acid oligomers. Starting with uracil-6-carboxylic acid (orotic acid), a peptide nucleic acid monomer compatible with Fmoc-based synthesis was prepared. This monomer then served as a convertible nucleobase whereupon treatment of the resin-bound methyl orotate containing hexamers with hydroxide or amines cleanly converted the ester to an orotic acid or orotamide-containing peptide nucleic acid. Peptide nucleic acid hexamers containing the C6-modified nucleobase hybridized to both poly(riboadenylic acid) and poly(deoxyriboadenylic acid) via triplex formation. Complexes formed with poly(riboadenylic acid) were more stable than those formed with poly(dexoyriboadenylic acid), as measured by temperature-dependent UV spectroscopy. However, both of these complexes were destabilized relative to the complexes formed by an unmodified peptide nucleic acid oligomers. Internal or doubly substituted hexamers are destabilized more strongly than a terminally substituted one, and the type of substitution (carboxamide, ester, carboxylic acid) affects the overall triplex stability. These results clearly show that incorporation of a C6-substituted uracil into polypyrimidine PNA is detrimental to triplex formation. We have also extended this chemistry to incorporate uracil-5-methylcarboxylate into a peptide nucleic acid hexamer. After on-resin conversion of the C5 ester to the 3-(N,N-dimethylamino)propylamide, significant stabilization of the triplex formed with poly(riboadenylic acid) was observed, which illustrates the compatibility of C5 substitution with peptide nucleic acid directed triple helix formation.

Stevioside analogs

Analogs of the glycoside stevioside are disclosed. These materials have the formula STR1 wherein R is a simple physiologically acceptable noncarbohydrate polar organic group. The analogs are sweet and find use as sweeteners.