149771-09-5

Usage

Uses

Used in Pharmaceutical Research:
ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE is used as an intermediate in the synthesis of various pharmaceutical compounds and research chemicals, contributing to the development of new drugs and therapies.
Used in Organic Synthesis:
In the field of organic synthesis, ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE serves as a key component in the creation of complex organic molecules, facilitating advancements in chemical research and product development.
Used in Antiviral Applications:
ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE is used as an antiviral agent for its ability to inhibit specific enzymes and pathways, potentially leading to the development of treatments for viral infections.
Used in Anticancer Applications:
ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE is used as an anticancer agent, leveraging its capacity to interfere with cellular processes in cancer cells, thus offering a potential therapeutic approach in oncology.

InChI:InChI=1/C8H8F3N3O2/c1-2-16-6(15)4-3-13-7(12)14-5(4)8(9,10)11/h3H,2H2,1H3,(H2,12,13,14)

Upstream product

• 571-55-1 ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate 
• 593-85-1 diguanidine carbonate 
• 593-85-1 guanidine carbonate 
• 4418-61-5 5-aminotetrazole 
• 154934-97-1 ethyl 2-hydroxy-4-trifluoromethylpyrimidine-5-carboxylate 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 1009378-96-4 3-methoxy-2-(2,2,2-trifluoro-acetyl)-acrylic acid ethyl ester 
• 187035-79-6 ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate 
• 593-87-3 guanidine acetic acid 
• 1048670-08-1 2-[1-ethoxy-meth-(Z)-ylidene]-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester 
• 2924-80-3 ethyl 4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate 

Downstream Products

• 910906-28-4 2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-4-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl ester 
• 149771-23-3 2-amino-4-trifluoromethyl-pyrimidine-5-carboxylic acid 

Relevant academic research and scientific papers

The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles

The interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino)prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate.

Traceless linker: Oxidative activation and displacement of a sulfur-based linker

The construction of small heterocycles using solid-phase chemistry is usually done through the use of a polar group to attach the compounds to the resin. These polar functionalities invariably become part of the structure and eventually limit the structure-activity relationships derived from these compounds. We have identified a method for overcoming some of these limitations. A sulfur-based linker has been identified that can serve not only as a point of attachment for a small heterocycle, but also as a means to introduce further diversity into the molecule. The linker remains inert until 'activated' by oxidation. A limiting amount of a nucleophile can then be used to cleave the molecule from the resin and introduce additional diversity into the molecule.

Reaction of 2-(ethoxymethylidene)-3-oxo carboxylic acid esters with tetrazol-5-amine

2-(Ethoxymethylidene)-3-oxo carboxylic acid esters reacted with tetrazol-5-amine to give ethyl 4-alkyl-2-azidopyrimidine-5-carboxylates capable of undergoing subsequent nucleophilic substitution of hydrogen on C6 or azido group. The reaction of ethyl 2-benzoyl-3-ethoxyprop-2-enoate with tetrazol-5-amine was accompanied by partial decomposition to afford a mixture of ethyl 3-oxo-3-phenylpropanoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate. Ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate was formed as a result of cyclization of diethyl 2-(ethoxymethylidene)propanedioate with tetrazol-5-amine.

IMIDAZOPYRIDINE AND IMIDAZOPYRIMIDINE DERIVATIVES

The present invention relates to imidazopyridine and imidazopyrimidine derivatives that act as cannabinoid receptor ligands, e.g., CB2 ligands. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

Structure-activity relationship studies of ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine- 5-carboxylate: An inhibitor of AP-1 and NF-κB mediated gene expression

Several analogues of ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine- 5-carboxylate (1) were synthesized and tested as inhibitors of AP-1 and NF-κB mediated transcriptional activation in Jurkat T cells. From our SAR work, ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))-N-methylamino]-4-(trifluoromethyl)- pyrimidine-5-carboxylate was identified as a novel and potent inhibitor.

Synthesis, antiviral (HSV-1) and antimycotic activities of ethyl or methyl 2,4-disubstituted 5-pyrimidinecarboxylates, 2,4-disubstituted 5-pyrimidinecarboxylic acids and 2,4-disubstituted pyrimidines

The synthesis of ethyl or methyl 4-substituted or unsubstituted 2-methylthio-5-pyrimidinecarboxylates 3 a-i and 8 o mainly by reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with 2-methylisothiourea is described. Also some ethyl 2-sub