6319-01-3

Basic information

• Product Name: ethyl 2-[(carbamoylamino)methylidene]-3-oxobutanoate
• CAS NO: 6319-01-3
• Molecular Formula: C₈H₁₂N₂O₄
• Molecular Weight: 200.1919
• Mol File: 6319-01-3.mol

Chemical Properties

• Boiling Point: 306.2°C at 760 mmHg
• Flash Point: 139°C
• Density: 1.219g/cm³
• Vapor Pressure: 0.000785mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: ethyl 2-[(carbamoylamino)methylidene]-3-oxobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-[(carbamoylamino)methylidene]-3-oxobutanoate(6319-01-3)
• EPA Substance Registry System: ethyl 2-[(carbamoylamino)methylidene]-3-oxobutanoate(6319-01-3)

Safety Data

• Hazardous Substances Data: 6319-01-3(Hazardous Substances Data)

Upstream product

• 141-97-9 ethyl acetoacetate 
• 122-51-0 orthoformic acid triethyl ester 
• 57-13-6 urea 
• 3788-94-1 2-ethoxymethylene-3-oxobutanoic acid ethyl ester 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 6214-65-9 5-acetyluracil 
• 6214-64-8 ethyl 4-methyl-2-oxo-1H-pyrimidine-5-carboxylate 
• 6214-64-8 ethyl 2-hydroxy-4-methylpyrimidine-5-carboxylate 
• 875296-11-0 5-acetyl-1,3-dibenzyluracil 
• 903594-08-1 1,3-bis(4-fluorobenzyl)-5-acetyluracil 
• 903594-07-0 1,3-bis(2-fluorobenzyl)-5-acetyluracil 
• 875296-12-1 4-(1,3-dibenzyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-2,4-dioxo-butyric acid methyl ester 
• 66373-46-4 2-hydrazino-4-methyl-pyrimidine-5-carboxylic acid ethyl ester 
• 188781-08-0 2-chloro-4-methylpyrimidine-5-carboxylic acid ethyl ester 
• 188781-13-7 2-chloro-4-methylpyrimidine-5-carbonyl chloride 
• 188781-10-4 2-chloro-4-methyl-pyrimidine-5-carboxylic acid 
• 15231-48-8 4-methyl-1H-pyrimidin-2-one 
• 13008-17-8 4-methyl-2-oxo-1H-pyrimidine-5-carboxylic acid 

Relevant articles and documents

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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.

Inhibitors of NF-kappaB and AP-1 gene expression: SAR studies on the pyrimidine portion of 2-chloro-4-trifluoromethylpyrimidine-5-[N-(3', 5'-bis(trifluoromethyl)phenyl)carboxamide].

We investigated the structure-activity relationship studies of N-[3, 5-bis(trifluoromethyl)phenyl][2-chloro-4-(trifluoromethyl)pyrimidin-5 -yl]carboxamide (1), an inhibitor of transcription mediated by both NF-kappaB and AP-1 transcription factors, with the goal of improving its potential oral bioavailability. Compounds were examined for cell-based activity, were fit to Lipinski's rule of 5, and were examined for potential gastrointestinal permeability using the intestinal epithelial cell line, Caco-2. Selected groups were substituted at the 2-, 4-, and 5-positions of the pyrimidine ring using solution-phase combinatorial methodology. The introduction of a fluorine in the place of 2-chlorine of 1 resulted in a compound with comparable activity. However, other substitutions at the 2-position resulted in a loss of activity. The trifluoromethyl group at the 4-position could be replaced with a methyl, ethyl, chlorine, or phenyl without a substantial loss of activity. The carboxamide group at the 5-position is critical for activity. If it was moved to the 6-position, the activity was lost. The 2-methyl analogue of 1 (81) showed comparable in vitro activity and improved Caco-2 permeability compared to 1.