113271-89-9

Basic information

• Product Name: ETHYL 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBOXYLATE
• Synonyms: ETHYL 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBOXYLATE;Ethyl 2-chloro-4-phenylpyrimidine-5-carboxylate ,97%
• CAS NO: 113271-89-9
• Molecular Formula: C₁₃H₁₁ClN₂O₂
• Molecular Weight: 262.69164
• Mol File: 113271-89-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBOXYLATE(113271-89-9)
• EPA Substance Registry System: ETHYL 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBOXYLATE(113271-89-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37
• Hazardous Substances Data: 113271-89-9(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow solid

InChI:InChI=1S/C13H11ClN2O2/c1-2-18-12(17)10-8-15-13(14)16-11(10)9-6-4-3-5-7-9/h3-8H,2H2,1H3

Upstream product

• 78317-69-8 1-Methyl-2-oxo-4-phenyl-5-ethoxycarbonyl-1,2,3,4-tetrahydropyrimidine 
• 188781-06-8 ethyl 2-hydroxy-4-phenylpyrimidine-5-carboxylate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 188781-04-6 ETHYL UREIDOMETHYLENE BENZOYLACETATE 
• 1116339-68-4 2-hydroxy-4-phenylpyrimidine-5-carboxylate 

Downstream Products

• 188781-11-5 2-chloro-4-phenylpyrimidine-5-carboxylic acid 
• 188936-37-0 ethyl 2-hydrazino-4-phenylpyrimidine-5-carboxylate 
• 188781-14-8 2-chloro-4-phenylpyrimidine-5-carbonyl chloride 

Relevant articles and documents

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.

Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions

Compounds having utility as anti-inflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are pyrimidine-containing compounds and, in one embodiment, are esters of the same. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition.

Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions

Compounds having utility as antinflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are pyrimidine- or pyrazine-containing compounds and, in one embodiment, are carboxyamides of the same. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition.

REACTIONS OF 1-METHYL-DERIVATIVES OF 2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINE WITH PHOSPHORUS PENTACHLORIDE AND PHOSPHORUS OXYCHLORIDE

In the reaction of 4-phenyl- and 4,6-diphenyl-1-methyl-2-oxo-5-ethoxycarbonyl-1,2,3,4-tetrahydropyrimidines with phosphorus pentachloride, oxidation and dealkylation takes place in addition to chlorination and as result one obtained 4-phenyl- and 4,6-diph