149771-09-5

Basic information

• Product Name: ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• Synonyms: BUTTPARK 37\18-35;ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)-5-PYRIMIDINECARBOXYLATE;ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMDINE-5-CARBOXYLATE;ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE;TIMTEC-BB SBB005526;2-amino-4-(trifluoromethyl)pyrimidine-5-carboxylic acid ethyl ester;ethyl 2-amino-4-(trifluoromethyl)-5-pyrimidinecarboxylate(SALTDATA: FREE);2-amino-4-(trifluoromethyl)-5-pyrimidinecarboxylic acid ethyl ester
• CAS NO: 149771-09-5
• Molecular Formula: C₈H₈F₃N₃O₂
• Molecular Weight: 235.16
• Mol File: 149771-09-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 179 °C
• Boiling Point: 366.7 °C at 760 mmHg
• Flash Point: 175.6 °C
• Appearance: /
• Density: 1.416 g/cm³
• Vapor Pressure: 1.44E-05mmHg at 25°C
• Refractive Index: 1.49
• Storage Temp.: 2-8°C(protect from light)
• PKA: 0.08±0.10(Predicted)
• CAS DataBase Reference: ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(149771-09-5)
• EPA Substance Registry System: ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(149771-09-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37/39-36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 149771-09-5(Hazardous Substances Data)

Usage

Description

ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE is a pyrimidine derivative with the molecular formula C8H8F3N3O2, featuring an ethyl ester group. This white to off-white solid is widely utilized in organic synthesis and pharmaceutical research, and is recognized for its potential as an antiviral and anticancer agent due to its enzyme and pathway inhibition capabilities.

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 
• 2924-80-3 ethyl 4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate 
• 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 

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 articles and documents

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.

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.

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.