83174-90-7

Usage

Structure

A heterocyclic compound containing a pyrimidine ring with two methyl groups (-CH3) at the 1st and 3rd positions, a formyl group (-CHO) at the 4th position, and two oxygen atoms (O) at the 2nd and 6th positions.

Functional Groups

Methyl groups, formyl group, and carbonyl groups.

Physical State

Likely a solid at room temperature, based on its molecular weight and structure.

Solubility

Soluble in organic solvents such as ethanol, methanol, and acetone, due to its nonpolar nature.

Reactivity

Can undergo various chemical reactions, such as condensation, substitution, and reduction, due to the presence of different functional groups.

Applications

Used as a building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals.

Synthesis

Can be synthesized through various methods, such as condensation reactions involving pyrimidine derivatives and aldehydes or ketones.

Stability

Relatively stable under normal conditions, but sensitive to strong acids, bases, and reducing agents.

Hazards

Potential irritant and harmful if inhaled, ingested, or comes into contact with the skin. Proper handling and storage are necessary to minimize risks.

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

Upstream product

• 13509-52-9 1,3,6-trimethyluracil 
• 134924-81-5 6-Dimethoxymethyl-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 36327-91-0 orotoaldehyde 
• 116705-39-6 6-(2-dimethylaminovinyl)-1,3-dimethyluracil 
• 21326-23-8 6-(dimethoxymethyl)uracil 
• 626-48-2 6-Methyluracil 
• 83174-91-8 1,3-dimethylorotaldehyde diethyl acetal 

Downstream Products

• 874-14-6 1,3-dimethyluracil 
• 134924-78-0 6-[Hydroxy-(5-methyl-furan-2-yl)-methyl]-1,3-dimethyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

PYRIDO[3,4-D]PYRIMIDINYL ACETAMIDE DERIVATIVES AS TRPA1 MODULATORS

Provided are pyrido[3,4-d]pyrimidinyl acetamide derivatives as Transient Receptor Potential Ankyrin (TRPA) modulators. In particular, the compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by Transient Receptor Potential Ankyrin 1 (TRPAl). Also provided herein are processes for preparing the compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders modulated by TRPA1. Formula (I).

Reactions of Uracils, 16. - Substituted 6-Vinyl-2,4(1H,3H)-pyrimidinediones in Cycloaddition and Michael-Type Reactions: Pyridopyrimidines, Pyrrolopyridines, and Quinazolines

Electron-rich 6-vinyl- and 6-(azavinyl)pyrimidinediones, such as 6-amino>- (1) and 6--1,3-dimethyl-2,4(1H,3H)-pyrimidinediones (8), undergo cycloaddition reactions with electron deficient olefins to give pyridopyrimidines (3a-e) and quinazolines (9a-c), respectively, after elimination of dimethylamine from the 1:1 cycloadducts and oxidative aromatization.With dimethyl acetylenedicarboxylate, pyrrolopyridines 5, 11, and 15 were obtained due to an initial Michael addition and subsequent ring transformation reaction.Stable Michael adducts were also obtained from reactions of 1 with azodicarboxylates.The stable adducts 6a-c were thermally converted into 8-(dimethylamino)theophylline (7). - Key Words: Pyridopyrimidines/ Pyrrolopyridines/ Quinazolines/ 6-Vinyl-2,4(1H,3H)-pyrimidinediones/ Cycloaddition

Model Chemistry for a Covalent Mechanism of Action of Orotidine 5'-Phosphate Decarboxylase

Orotidine 5'-phosphate decarboxylase (ODase) catalyzes the conversion of orotidylate to uridylate, the last step in the de novo biosynthesis of pyrimidine nucleotides.Model reactions are described that support a covalent catalytic mechanism for this enzyme in which, following protonation of the carboxyl group of orotidylic acid, an active-site nucleophile undergoes a Michael addition to the C-5 position.This covalent complex breaks down via an acid-base-catalyzed decarboxylative elimination reaction to give uridylate and CO2 (Scheme II).The enzyme mechanism is modeled in two parts, the Michael addition reaction and the decarboxylative elimination.Bisulfite is shown to undergo a Michael addition to N,N-dimethylorotaldehyde and at room temperature to N,N-dimethyl-6-acetyluracil, both models for the activated form of orotidylate, the substrate for ODase (6 -> 7).In a separate study, (+/-)-1,3-dimethyl-r-5-(methylthio)-5-methyl-trans-6-carboxyl-5,6-dihydrouracil (15) was prepared as a model for the ODase-orotidylate covalent complex.Activation by methylation of the sulfide (as a model for enzyme-catalyzed protonation) leads to instantaneous decarboxylative elimination at room temperature.When the corresponding ester (9c) is methylated, the dimethylsulfonium salt (16b) can be isolated, which upon ester hydrolysis gives the decarboxylative elimination product.These model studies support the Michael addition-decarboxylative elimination mechanism in favor of a noncovalent mechanism previously reported (Beak, P.; Siegel, B.J.Am.Chem.Soc. 1976, 98, 3601).