188781-08-0

Basic information

• Product Name: ETHYL 2-CHLORO-4-METHYLPYRIMIDINE-5-CARBOXYLATE
• Synonyms: ETHYL 2-CHLORO-4-METHYLPYRIMIDINE-5-CARBOXYLATE;Ethyl 2-chloro-4-methylpyrimidine-5-carboxylate ,97%;2-Chloro-5-(ethoxycarbonyl)-4-methylpyrimidine;2-Chloro-4-methyl-5-pyrimidinecarboxylic acid ethyl ester;2-Chloro-5-(ethoxycarbonyl)-4-methylpyrimidine, 2-Chloro-5-(ethoxycarbonyl)-4-methyl-1,3-diazine;5-Pyrimidinecarboxylic acid, 2-chloro-4-methyl-, ethyl ester
• CAS NO: 188781-08-0
• Molecular Formula: C₈H₉ClN₂O₂
• Molecular Weight: 200.62226
• Product Categories: pyrimidine;Heterocycle-Pyrimidine series
• Mol File: 188781-08-0.mol

Chemical Properties

• Boiling Point: 302.7 °C at 760 mmHg
• Flash Point: 136.9 °C
• Appearance: /
• Density: 1.265
• Vapor Pressure: 0.000972mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.56±0.29(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: ETHYL 2-CHLORO-4-METHYLPYRIMIDINE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-CHLORO-4-METHYLPYRIMIDINE-5-CARBOXYLATE(188781-08-0)
• EPA Substance Registry System: ETHYL 2-CHLORO-4-METHYLPYRIMIDINE-5-CARBOXYLATE(188781-08-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 188781-08-0(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

It is an active pharmaceutical intermediates.

InChI:InChI=1/C8H9ClN2O2/c1-3-13-7(12)6-4-10-8(9)11-5(6)2/h4H,3H2,1-2H3

Upstream product

• 6214-64-8 ethyl 2-hydroxy-4-methylpyrimidine-5-carboxylate 
• 6319-01-3 ethyl 2-acetyl-3-ureido-2-propenoate 
• 141-97-9 ethyl acetoacetate 
• 17994-55-7 6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 
• 6214-64-8 6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic acid ethyl ester 

Downstream Products

• 108123-81-5 2-benzylamino-4-methylpyrimidine-5-carboxylic acid ethyl ester 
• 81633-29-6 2-amino-4-methylpyrimidine-5-carboxylic acid ethyl ester 
• 1150103-18-6 N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide 
• 1150103-19-7 N-{4-[(5-formyl-4-methyl-2-pyrimidinyl)oxy]phenyl}methanesulfonamide 
• 1150103-00-6 5-({[(3-fluorophenyl)(1-{[4-methyl-2-({4-[(methylsulfonyl)amino]phenyl}oxy)-5-pyrimidinyl]methyl}-4-piperidinyl)amino]carbonyl}amino)-2-pyridinecarboxamide 
• 1150103-17-5 ethyl 4-methyl-2-({4-[(methylsulfonyl)amino]phenyl}oxy)-5-pyrimidinecarboxylate 
• 188781-13-7 2-chloro-4-methylpyrimidine-5-carbonyl chloride 
• 66373-46-4 2-hydrazino-4-methyl-pyrimidine-5-carboxylic acid ethyl ester 
• 188781-10-4 2-chloro-4-methyl-pyrimidine-5-carboxylic acid 

Relevant articles and documents

NOVEL COMPOUNDS AS REARRANGED DURING TRANSFECTION (RET) INHIBITORS

This invention relates to novel compounds which are inhibitors of the Rearranged during Transfection (RET) kinase, to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in combination, for the normalization of gastrointestinal sensitivity, motility and/or secretion and/or abdominal disorders or diseases and/or treatment related to diseases related to RET dysfunction or where modulation of RET activity may have therapeutic benefit including but not limited to all classifications of irritable bowel syndrome (IBS) including diarrhea-predominant, constipation-predominant or alternating stool pattern, functional bloating, functional constipation, functional diarrhea, unspecified functional bowel disorder, functional abdominal pain syndrome, chronic idiopathic constipation, functional esophageal disorders, functional gastroduodenal disorders, functional anorectal pain, inflammatory bowel disease, proliferative diseases such as non-small cell lung cancer, hepatocellular carcinoma, colorectal cancer, medullary thyroid cancer, follicular thyroid cancer, anaplastic thyroid cancer, papillary thyroid cancer, brain tumors, peritoneal cavity cancer, solid tumors, other lung cancer, head and neck cancer, gliomas, neuroblastomas, Von Hippel-Lindau Syndrome and kidney tumors, breast cancer, fallopian tube cancer, ovarian cancer, transitional cell cancer, prostate cancer, cancer of the esophagus and gastroesophageal junction, biliary cancer, adenocarcinoma, and any malignancy with increased RET kinase activity.

Synthesis of 4-aminoquinoline - Pyrimidine hybrids as potent antimalarials and their mode of action studies

One of the most viable options to tackle the growing resistance to the antimalarial drugs such as artemisinin is to resort to synthetic drugs. The multi-target strategy involving the use of hybrid drugs has shown promise. In line with this, new hybrids of

PYRIMIDINE AMIDE COMPOUNDS

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of inflammatory diseases and disorders such as, for example, asthma and COPD.

Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity

A series of pyrimidine derivatives bearing amine substituents at C-2 position were obtained from Biginelli 3,4-dihydropyrimidin-2(1H)-ones and the effect of structural variation on anti-TB activity against Mycobacterium tuberculosis H37Rv strai

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.