3177-20-6

Basic information

• Product Name: Methyl2,4-Dichloropyrimidine-5-carboxylate
• Synonyms: Methyl 2,4-dichloropyrimidine-5-carboxylate, GC 97%;Methyl 2,4-dichloro-5-pyrimidinecarboxylate;5-PyriMidinecarboxylic acid, 2,4-dichloro-, Methyl ester;Methyl 2,4-dichloropyrimidine-5-carboxylate 97%;2,4-Dichloropyrimidine-5-carboxylicacid methyl ester
• CAS NO: 3177-20-6
• Molecular Formula: C₆H₄Cl₂N₂O₂
• Molecular Weight: 207.02
• Product Categories: pharmacetical;Heterocycle-Pyrimidine series
• Mol File: 3177-20-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 30-34℃
• Boiling Point: 299.3 °C at 760 mmHg
• Flash Point: 110℃
• Appearance: /
• Density: 1.503 g/cm³
• Vapor Pressure: 0.0012mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -4.55±0.29(Predicted)
• CAS DataBase Reference: Methyl2,4-Dichloropyrimidine-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl2,4-Dichloropyrimidine-5-carboxylate(3177-20-6)
• EPA Substance Registry System: Methyl2,4-Dichloropyrimidine-5-carboxylate(3177-20-6)

Safety Data

• Hazard Codes: Xn
• Statements: 26-36/37/38-22
• Safety Statements: 26-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3177-20-6(Hazardous Substances Data)

Usage

General Description

Methyl 2,4-Dichloropyrimidine-5-carboxylate is a chemical compound with the molecular formula C6H4Cl2N2O2. It is a synthetic intermediate used in the production of pharmaceuticals, agrochemicals, and other organic compounds. Methyl2,4-Dichloropyrimidine-5-carboxylate is typically used as a building block for the synthesis of various pyrimidine derivatives, which have diverse applications in the pharmaceutical and agricultural industries. It is important to handle and store this chemical with care, as it can be hazardous if not properly managed. Methyl 2,4-Dichloropyrimidine-5-carboxylate is a valuable chemical reagent that is widely utilized in organic synthesis for the production of a wide range of compounds with important commercial and industrial applications.

InChI:InChI=1/C6H4Cl2N2O2/c1-12-5(11)3-2-9-6(8)10-4(3)7/h2H,1H3

Upstream product

• 67-56-1 methanol 
• 2972-52-3 2,4-dichloropyrimidine-5-carbonyl chloride 
• 42821-92-1 methyl 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 

Downstream Products

• 71406-78-5 ethyl 4-amino-2-chloropyrimidine-5-carboxylate 
• 1374639-78-7 N,N‐dimethyl‐7‐cyclopentyl‐2‐{[5‐(4-tert-butoxycarbonylpiperazin‐1‐yl)pyridin‐2‐yl]amino}‐7H‐pyrrolo[2,3‐d]pyrimidine‐6‐carboxamide 
• 1612783-19-3 C₃₁H₄₀N₈O₂ 
• 1612782-97-4 (S)-9-amino-N-(4-fluorobenzyl)-8-oxo-2,7,13-triaza-1(2,4)-pyrimidinacyclotridecaphane-1-carboxamide 
• 1609533-88-1 C₁₃H₁₂ClN₃O₂S 
• 1609534-64-6 C₁₉H₁₇FN₆O₂ 
• 1609533-92-7 C₁₉H₁₆FN₅O₃ 
• 1609533-74-5 C₁₇H₂₁N₅O₃S 
• 1609533-90-5 C₁₇H₂₀N₄O₄S 
• 1609533-89-2 C₁₇H₂₀N₄O₂S 
• 1609533-91-6 C₁₃H₁₁ClN₄O₃ 
• 1493764-08-1 2-(butylamino)-4-[(4-hydroxycyclohexyl)amino]-N-{[4-(1H-imidazol-1-yl)phenyl]methyl}pyrimidine-5-carboxamide 

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.

PYRIMIDINE COMPOUNDS FOR THE TREATMENT OF CANCER

Compounds of Formula I or II: are described, along with pharmaceutical compositions containing the same and methods of using such compounds for the treatment of cancer.

Discovery of Mer specific tyrosine kinase inhibitors for the treatment and prevention of thrombosis

The role of Mer kinase in regulating the second phase of platelet activation generates an opportunity to use Mer inhibitors for preventing thrombosis with diminished likelihood for bleeding as compared to current therapies. Toward this end, we have discovered a novel, Mer kinase specific substituted-pyrimidine scaffold using a structure-based drug design and a pseudo ring replacement strategy. The cocrystal structure of Mer with two compounds (7 and 22) possessing distinct activity have been determined. Subsequent SAR studies identified compound 23 (UNC2881) as a lead compound for in vivo evaluation. When applied to live cells, 23 inhibits steady-state Mer kinase phosphorylation with an IC50 value of 22 nM. Treatment with 23 is also sufficient to block EGF-mediated stimulation of a chimeric receptor containing the intracellular domain of Mer fused to the extracellular domain of EGFR. In addition, 23 potently inhibits collagen-induced platelet aggregation, suggesting that this class of inhibitors may have utility for prevention and/or treatment of pathologic thrombosis.