1016636-76-2

Basic information

• Product Name: 6-broMo-2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one
• Synonyms: 6-broMo-2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-on;6-broMo-2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one;Pyrido[2,3-d]pyriMidin-7(8H)-one, 6-broMo-2-chloro-8-cyclopentyl-5-Methyl-;6-broMo-2-chloro-8-cyclopentyl-5-;6-BroMo-2-chloro-8-cyclopentyl-5-Methyl-8H-pyrido[2,3-d]pyriMidin-7-one;6-bromo-2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one(For Palbociclib);6-bromo-2-chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one;PALBOCI
• CAS NO: 1016636-76-2
• Molecular Formula: C13H13BrClN3O
• Molecular Weight: 342.61882
• EINECS: 1592732-453-0
• Product Categories: Anticancer;Palbociclib;PD 0332991
• Mol File: 1016636-76-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 468.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.645±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly, Sonicated
• PKA: -0.61±0.20(Predicted)
• CAS DataBase Reference: 6-broMo-2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-broMo-2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one(1016636-76-2)
• EPA Substance Registry System: 6-broMo-2-chloro-8-cyclopentyl-5-Methylpyrido[2,3-d]pyriMidin-7(8H)-one(1016636-76-2)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN2811
• Hazardous Substances Data: 1016636-76-2(Hazardous Substances Data)

Usage

Description

6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one is a complex organic compound characterized by its unique molecular structure. It is a derivative of pyrido[2,3-d]pyrimidin-7(8H)-one, featuring a cyclopentyl group at the 8th position, a methyl group at the 5th position, a bromine atom at the 6th position, and a chlorine atom at the 2nd position. 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one holds potential applications in the pharmaceutical industry due to its ability to inhibit specific protein kinases, such as CDK4 and CDK6.

Uses

Used in Pharmaceutical Industry:
6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one is used as a precursor to prepare pyridino[2,3-d]pyrimidin-7(8H)-one derivatives, which act as CDK4 and/or CDK6 inhibitors. These inhibitors are crucial in the treatment of various diseases, particularly those involving uncontrolled cell proliferation, such as cancer. By targeting CDK4 and CDK6, these derivatives can potentially halt the progression of the disease and provide therapeutic benefits to patients.

InChI:InChI=1S/C13H13BrClN3O/c1-7-9-6-16-13(15)17-11(9)18(12(19)10(7)14)8-4-2-3-5-8/h6,8H,2-5H2,1H3

Upstream product

• 23755-73-9 triethyl bromophosphonoacetate 
• 1244949-62-9 C₁₁H₁₄ClN₃O 
• 733039-20-8 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine 
• 1003-03-8 Cyclopentamine 
• 1013916-37-4 2-chloro-5-methyl-8-cyclopentylpyridin[2,3-d]pyrimidin-8-hydro-7-one 

Downstream Products

• 571188-82-4 tert?butyl 4?(6?((6?bromo?8?cyclopentyl?5?methyl?7?oxo?7,8?dihydropyrido[2,3?d]pyrimidin?2?yl)amino)pyridin?3?yl)piperazine?1?carboxylate 
• 866084-31-3 tert?butyl 4?(6?((6?(1?butoxyvinyl)?8?cyclopentyl?5?methyl?7?oxo?7,8?dihydropyrido[2,3?d]pyrimidin?2?yl)amino)pyridin?3?yl)piperazine?1?carboxylate 
• 571190-30-2 PD 0332991 
• 1651214-74-2 4-[6-(6-acetyl-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)pyridine-3-yl]piperazine-1-carboxylic acid tert-butyl ester 
• 850628-81-8 6-acetyl-8-cyclopentyl-5-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one 
• 827022-33-3 6-acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one isethionate 
• 827022-33-3 PD 0332991 isethionate 

Relevant articles and documents

Preparation method of palbociclib intermediate

The invention discloses a preparation method of a palbociclib intermediate, which comprises the following steps: by using 2-chlorine-8-cyclopentyl-5-methylpyrido [2, 3-D] pyrimidine -7 (8H) -ketone as a raw material, carrying out NBS bromination and cooling crystallization centrifugation under the catalysis of oxalic acid and acetic anhydride to obtain 6-bromine-2-chlorine-8-cyclopentyl-5-methylpyrido [2, 3-D] pyrimidine -7 (8H) -ketone; meanwhile, waste liquid generated in the preparation process is fully reutilized, three wastes are reduced, and the preparation method which is high in quality, low in cost, environmentally friendly and suitable for industrial production is provided.

Preparation method of palbociclib intermediate

The invention discloses a preparation method of a palbociclib intermediate. The method comprises the following steps: preparing 5-bromine-2-chloro-N-cyclopentylamine pyrimidine-4 amine from 5-bromine-2,4-dichloropyrimidine and cyclopentylamine by taking solvents such as dichloromethane and water as solvents and taking inorganic base as an acid-binding agent; with DIEA as an acid-binding agent, DMF as a solvent and TBAB as a phase transfer catalyst, in the presence of water, catalyzing with a trace amount of palladium, and carrying out normal hexane reflux dehydration; further subjecting the acetic anhydride to dehydration cyclization, such that 2-chloro-8-cyclopentyl-5-methylpyridino[2,3-D]pyrimidine-7-(8H)-ketone is obtained; and reacting the obtained compound with NBS (N-bromosuccinimide) in acetonitrile to obtain the 6-bromo-2-chloro-8-cyclopentyl-5-methylpyridino[2, 3-D]pyrimidine-7(8H)-ketone. The method is mild in reaction, simple and convenient to operate, recyclable in solvent, less in environmental pollution, high in yield, low in cost, high in product quality and suitable for industrial production.

Discovery of 5-methylpyrimidopyridone analogues as selective antimycobacterial agents

With the emergence of multidrug-resistant strains of Mycobacterium tuberculosis (MDR-TB) and extensive drug-resistant strains (XDR-TB), there is an urgent need to develop novel drugs for the treatment of tuberculosis. Here, we designed and synthesized a series of 5-methylpyrimidopyridone analogues as potential antitubercular agents. The most potent compound 6q exhibited a MIC value of 4 μM in vitro against Mycobacterium tuberculosis. The antitubercular activities of the synthesized compounds were impacted by the amantadine and 2-chlorophenyl groups, and were enhanced by the presence of 3-methyl(4-dimethylamino)piperidinylphenyl. Molecular modeling and binding studies suggest that PknB is the potential molecular target of 5-methylpyrimidopyridone compounds. This study provides insights for the future development of new antimycobacterial agents with novel mechanisms of action.