104711-65-1

Basic information

• Product Name: 4-Chloro-2-cyano-6-methylpyrimidine
• Synonyms: 4-Chloro-2-cyano-6-methylpyrimidine;4-Chloro-2-cyano-6-methylpyridine;4-Chloro-6-Methylpicolinonitrile
• CAS NO: 104711-65-1
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.583
• Mol File: 104711-65-1.mol

Chemical Properties

• Melting Point: 78-79 °C
• Boiling Point: 250.1°C at 760 mmHg
• Flash Point: 105.1°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 0.0221mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.72±0.10(Predicted)
• CAS DataBase Reference: 4-Chloro-2-cyano-6-methylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-cyano-6-methylpyrimidine(104711-65-1)
• EPA Substance Registry System: 4-Chloro-2-cyano-6-methylpyrimidine(104711-65-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 104711-65-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-cyano-6-methylpyrimidine is used as a key intermediate in the synthesis of various drugs. Its unique structural features make it a valuable component in the development of new medicinal compounds, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Agrochemical Industry:
4-Chloro-2-cyano-6-methylpyrimidine is also utilized in the production of pesticides. Its incorporation into agrochemical formulations can enhance the effectiveness of these products, providing farmers with more potent and targeted pest control solutions.
Used in Chemical Synthesis:
As a pyrimidine derivative, 4-Chloro-2-cyano-6-methylpyrimidine is employed in the synthesis of a wide range of chemical compounds. Its versatility in chemical reactions makes it an essential building block in the creation of new molecules with potential applications in various industries.

InChI:InChI=1/C7H5ClN2/c1-5-2-6(8)3-7(4-9)10-5/h2-3H,1H3

Upstream product

• 5470-66-6 2-methyl-4-nitropyridine N-oxide 
• 3678-63-5 4-chIoro-2-methylpyridine 
• 696-08-2 4-chloro-2-picoline-N-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Downstream Products

• 339586-00-4 1-(4-chloro-6-methylpyridin-2-yl)ethan-1-one 
• 1375338-67-2 2-(4-methoxy-6-methylpyridin-2-yl)-4-(3-methoxyphenyl)quinazoline 
• 1375324-82-5 2-(4-chloro-6-methylpyridin-2-yl)-4-(3-methoxyphenyl)quinazoline 
• 1375320-24-3 2-(4,6-dimethylpyridin-2-yl)-4-(3-methoxyphenyl)quinazoline 
• 1396337-04-4 N-(5-fluoropyridin-2-yl)-6-methyl-4-(pyrimidin-5-yloxy)picolinamide 

Relevant articles and documents

Development and kilogram-scale synthesis of mGlu5 negative allosteric modulator VU0424238 (auglurant)

This communication details the kilogram-scale synthesis of N-(5-fluoropyridin-2-yl)-6-methyl-4-(pyrimidin-5-yloxy)picolinamide (VU0424238, auglurant), a novel mGlu5 negative allosteric modulator (NAM) developed as an alternative treatment for depression. The process highlights a challenging pyridine N-oxidation sequence, an SNAr reaction, and the elimination of all chromatography steps (required in the medicinal chemistry route) with replacement by highly efficient recrystallizations (save one silica plug). The improved process was utilized for the preparation of a 1.2 kg toxicology batch, as well as a 2.82 kg GMP batch to support the Phase I trial, in very high purity (99.8%).

BCL-2 INHIBITORS AND THEIR USE AS PHARMACEUTICALS

The disclosure is directed to, in part, to BCL-2 inhibitors, pharmaceutical compositions comprising the same, as well as methods of their use and preparation.

Discovery of N-(5-Fluoropyridin-2-yl)-6-methyl-4-(pyrimidin-5-yloxy)picolinamide (VU0424238): A Novel Negative Allosteric Modulator of Metabotropic Glutamate Receptor Subtype 5 Selected for Clinical Evaluation

Preclinical evidence in support of the potential utility of mGlu5 NAMs for the treatment of a variety of psychiatric and neurodegenerative disorders is extensive, and multiple such molecules have entered clinical trials. Despite some promising results from clinical studies, no small molecule mGlu5 NAM has yet to reach market. Here we present the discovery and evaluation of N-(5-fluoropyridin-2-yl)-6-methyl-4-(pyrimidin-5-yloxy)picolinamide (27, VU0424238), a compound selected for clinical evaluation. Compound 27 is more than 900-fold selective for mGlu5 versus the other mGlu receptors, and binding studies established a Ki value of 4.4 nM at a known allosteric binding site. Compound 27 had a clearance of 19.3 and 15.5 mL/min/kg in rats and cynomolgus monkeys, respectively. Imaging studies using a known mGlu5 PET ligand demonstrated 50% receptor occupancy at an oral dose of 0.8 mg/kg in rats and an intravenous dose of 0.06 mg/kg in baboons.

IMIDAZOPYRIDINE EZH2 INHIBITORS

The present invention relates to imidazopyridines of general formula (I), to a method for their preparation, to intermediates for their preparation, to pharmaceutical compositions comprising at least one of those compounds, and to the use thereof.

SUBSTITUTED 4-ALKOXYPICOLINAMIDE ANALOGS DS MGLUR5 NEGATIVE ALLOSTERIC MODULATORS

Disclosed are negative allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with glutamate dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

6-ALKYL-N-(PYRIDIN-2-YL)-4-ARYLOXYPICOLINAMIDE ANALOGS AS MGLUR5 NEGATIVE ALLOSTERIC MODULATORS AND METHODS OF MAKING AND USING THE SAME

Disclosed are negative allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with glutamate dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

2 - (PYRIDIN- 2 -YL) -QUINAZOLINE DERIVATIVES AND THEIR USE AS MICROBICIDES

Compounds of formula I wherein the other substituents R1, R2, R3, R4, R5 and R6 are as defined in claim 1, and their use as microbicides.

A simple procedure for the preparation of 2-cyano-4-chloropyridines

Figure represented. 4-Nitro-pyridine-N-oxides are reacted with ethylchloroformate and trimethylsilyl cyanide to give 4-chloro-2-cyanopyridine.

Oxime O-ether compounds and fungicides for agricultural and horticultural use

The present invention relates to novel oxime O-ether compounds represented by a general formula [I]; wherein R1represents C1-6alkyl, C3-6cycloalkyl, C1-6alkoxy, etc., m represents an integer of 1 to 4, R2/