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

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

Uses

Used in Pharmaceutical Industry:
Methyl 2,4-Dichloropyrimidine-5-carboxylate is used as a key intermediate for the synthesis of pyrimidine-based pharmaceuticals, contributing to the development of drugs with therapeutic properties. Its role in creating pyrimidine derivatives allows for the exploration of new drug candidates with potential applications in treating various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 2,4-Dichloropyrimidine-5-carboxylate is utilized as a precursor in the synthesis of pyrimidine-based agrochemicals, such as herbicides and insecticides. Its involvement in the development of these compounds helps address challenges in agriculture, including pest control and crop protection, ultimately contributing to increased crop yields and food security.
Used in Organic Synthesis:
Methyl 2,4-Dichloropyrimidine-5-carboxylate is employed as a versatile reagent in organic synthesis, enabling the production of a wide range of compounds with significant commercial and industrial applications. Its use in this field highlights its importance in the synthesis of various organic compounds, further expanding its utility across different industries.

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 
• 1073438-02-4 methyl 2-chloro-4-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenylamino]-pyrimidine-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 

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.

THERAPUETIC USES OF SELECTED PYRIMIDINE COMPOUNDS WITH ANTI-MER TYROSINE KINASE ACTIVITY

Uses of pyrimidines with anti-Mer tyrosine kinase activity as anti-infective agents, immunostimulatory and immunomodulatory agents, anti-cancer agents (including against MerTK -/- tumors and ITD and TKD mutant forms of Acute Myeloid Leukemia (AML)), and as adjunctive agents in combination with chemotherapeutic, radiation or other standard of care for neoplasms.

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.

PYRIMIDINE COMPOUNDS FOR THE TREATMENT OF CANCER

Described are compounds of Formula I or Formula II: wherein: ring A is a 5- or 6-membered heteroaryl group; dashed lines are optional double bonds; X is N or O; Y is a carbon atom or an S or N heteroatom in ring A in any suitable location; and substituents are as given herein. Compositions containing the same and methods of using the same in treating cancers such as acute lymphoblastic leukemia are also described.

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.

Design and pharmacological evaluation of PF-4840154, a non-electrophilic reference agonist of the TrpA1 channel

TrpA1 is an ion channel involved in nociceptive and inflammatory pain. It is implicated in the detection of chemical irritants through covalent binding to a cysteine-rich intracellular region of the protein. While performing an HTS of the Pfizer chemical collection, a class of pyrimidines emerged as a non-reactive, non-covalently binding family of agonists of the rat and human TrpA1 channel. Given the issues identified with the reference agonist Mustard Oil (MO) in screening, a new, non-covalently binding agonist was optimized and proved to be a superior agent to MO for screening purposes. Compound 16a (PF-4840154) is a potent, selective agonist of the rat and human TrpA1 channel and elicited TrpA1-mediated nocifensive behaviour in mouse.

4-Amino-2-cyanopyrimidines: Novel scaffold for nonpeptidic cathepsin S inhibitors

We describe here a novel 4-amino-2-cyanopyrimidine scaffold for nonpeptidomimetic cathepsin S selective inhibitors. Some of the synthesized compounds have sub-nanomolar potency and high selectivity toward cathepsin S along with promising pharmacokinetic a

2,4-Dithi(oxo)-pyrimidin-5-yl compounds bearing a tricyclic substituent useful as P2 purinoceptor antagonists

PCT No. PCT/SE98/01240 Sec. 371 Date Sep. 30, 1998 Sec. 102(e) Date Sep. 30, 1998 PCT Filed Jun. 25, 1998 PCT Pub. No. WO99/02501 PCT Pub. Date Jan. 21, 1999The invention relates to new pharmaceutically active compounds which are P2-purinoceptor 7-transmembrane (TM) G-protein coupled receptor antagonists, compositions containing them and processes for their preparation.