51940-64-8

Basic information

• Product Name: ethyl 2,4-dichloropyrimidine-5-carboxylate
• Synonyms: ethyl 2,4-dichloropyrimidine-5-carboxylate;Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate;2,4-Dichloro-5-pyrimidinecarboxylic acid ethyl ester;2,4-Dichloropyrimidine-5-carboxylic acid ethyl ester;Ethyl 2,4-dichloro-5 pyrimidine carboxylic acid;5-PyriMidinecarboxylic acid, 2,4-dichloro-, ethyl ester;2,4-Dichlo-5-(ethoxycarbonyl)pyrimidine, 2,4-Dichlo-5-(ethoxycarbonyl)-1,3-diazine;2,4-dichloropyriMidine-5-carboxylate
• CAS NO: 51940-64-8
• Molecular Formula: C₇H₆Cl₂N₂O₂
• Molecular Weight: 221.04074
• EINECS: 257-531-8
• Product Categories: Acids and Derivatives;Heterocycles;pharmacetical;Heterocycle-Pyrimidine series
• Mol File: 51940-64-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 36-37℃
• Boiling Point: 145°C/11mmHg(lit.)
• Flash Point: 142.4 °C
• Appearance: White/Powder
• Density: 1.433
• Vapor Pressure: 0.000549mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 0-10°C
• PKA: -4.47±0.29(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: ethyl 2,4-dichloropyrimidine-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,4-dichloropyrimidine-5-carboxylate(51940-64-8)
• EPA Substance Registry System: ethyl 2,4-dichloropyrimidine-5-carboxylate(51940-64-8)

Safety Data

• Hazardous Substances Data: 51940-64-8(Hazardous Substances Data)

Usage

Description

Ethyl 2,4-dichloropyrimidine-5-carboxylate is an organic compound that serves as a crucial intermediate in the synthesis of various chemical products. It is characterized by its chemical structure, which includes a pyrimidine ring with two chlorine atoms at the 2nd and 4th positions and a carboxylate group attached to the 5th position. This structure endows it with versatile reactivity and potential applications in different industries.

Uses

Used in Organic Synthesis:
Ethyl 2,4-dichloropyrimidine-5-carboxylate is used as a key intermediate for the synthesis of various organic compounds. Its unique chemical structure allows for further functionalization and the creation of a wide range of products with diverse applications.
Used in Agrochemical Industry:
In the agrochemical industry, ethyl 2,4-dichloropyrimidine-5-carboxylate is used as a starting material for the development of new pesticides and other agricultural chemicals. Its reactivity and structural features make it a valuable component in the design and synthesis of effective and targeted agrochemicals.
Used in Pharmaceutical Industry:
Ethyl 2,4-dichloropyrimidine-5-carboxylate is employed as an important intermediate in the pharmaceutical industry for the synthesis of various drugs. Its chemical properties enable the development of new therapeutic agents with potential applications in treating a range of medical conditions.
Used in Dyestuff Industry:
In the dyestuff industry, ethyl 2,4-dichloropyrimidine-5-carboxylate is used as a raw material for the production of different types of dyes. Its structural characteristics contribute to the development of novel dyes with improved properties, such as enhanced color strength and stability.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 794, 1942 DOI: 10.1021/ja01256a016

InChI:InChI=1/C7H6Cl2N2O2/c1-2-13-6(12)4-3-10-7(9)11-5(4)8/h3H,2H2,1H3

Upstream product

• 28485-17-8 5-carbethoxyuracil 
• 5909-24-0 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester 
• 144-55-8 sodium hydrogencarbonate 
• 28485-17-8 5-carbethoxyuracil 
• 64-17-5 ethanol 
• 2972-52-3 2,4-dichloropyrimidine-5-carbonyl chloride 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 23945-44-0 2,4-dihydroxypyrimidine-5-carboxylic acid 
• 92264-75-0 2,4-dioxohexahydropyrimidine-5-carboxylic acid 
• 1428760-91-1 ethyl 2,4-dioxohexahydropyrimidine-5-carboxylate 

Downstream Products

• 65754-04-3 6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid 
• 55996-27-5 2-ethoxy-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 4595-61-3 pyrimidine-5-carboxylic acid 
• 71406-78-5 ethyl 4-amino-2-chloropyrimidine-5-carboxylate 
• 863028-78-8 ethyl 2-chloro-4-(3-isopropylanilino)pyrimidine-5-carboxylate 
• 227449-13-0 ethyl 2-chloro-4-(3-methoxyanilino)pyrimidine-5-carboxylate 
• 227449-11-8 ethyl 2-chloro-4-(3-trifluoromethylanilino)pyrimidine-5-carboxylate 
• 227449-05-0 ethyl 2-chloro-4-(4-methylanilino)pyrimidine-5-carboxylate 
• 280581-48-8 4-phenylamino-2-chloropyrimidine-5-carboxylic acid ethyl ester 
• 227449-09-4 ethyl 2-chloro-4-(3-methylanilino)pyrimidine-5-carboxylate 
• 863028-77-7 ethyl 2-chloro-4-(3-ethylanilino)pyrimidine-5-carboxylate 
• 227449-12-9 ethyl 2-chloro-4-(3-cyanoanilino)pyrimidine-5-carboxylate 
• 227449-10-7 ethyl 2-chloro-4-(2-methylanilino)pyrimidine-5-carboxylate 
• 227449-16-3 ethyl 4-(3-bromoanilino)-2-chloropyrimidine-5-carboxylate 

Relevant articles and documents

Discovery of Macrocyclic Pyrimidines as MerTK-Specific Inhibitors

Macrocycles have attracted significant attention in drug discovery recently. In fact, a few de novo designed macrocyclic kinase inhibitors are currently in clinical trials with good potency and selectivity for their intended target. In this study, we successfully engaged a structure-based drug design approach to discover macrocyclic pyrimidines as potent Mer tyrosine kinase (MerTK)-specific inhibitors. An enzyme-linked immunosorbent assay (ELISA) in 384-well format was employed to evaluate the inhibitory activity of macrocycles in a cell-based assay assessing tyrosine phosphorylation of MerTK. Through structure–activity relationship (SAR) studies, analogue 11 [UNC2541; (S)-7-amino-N-(4-fluorobenzyl)-8-oxo-2,9,16-triaza-1(2,4)-pyrimidinacyclohexadecaphane-1-carboxamide] was identified as a potent and MerTK-specific inhibitor that exhibits sub-micromolar inhibitory activity in the cell-based ELISA. In addition, an X-ray structure of MerTK protein in complex with 11 was resolved to show that these macrocycles bind in the MerTK ATP pocket.

PHARMACEUTICAL COMPOUNDS

The present invention relates to compounds that are useful as inhibitors of the activity of Wee-1 kinase. The present invention also relates to pharmaceutical compositions comprising these compounds and to methods of using these compounds in the treatment of cancer and methods of treating cancer.

2,4-Pyrimidinediamine Compounds and Their Uses

The present invention provides 2,4-pyrimidinediamine compounds that inhibit the IgE and/or IgG receptor signaling cascades that lead to the release of chemical mediators, intermediates and methods of synthesizing the compounds and methods of using the compounds in a variety of contexts, including in the treatment and prevention of diseases characterized by, caused by or associated with the release of chemical mediators via degranulation and other processes effected by activation of the IgE and/or IgG receptor signaling cascades.