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

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

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

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

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 
• 827022-33-3 PD 0332991 isethionate 
• 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 

Relevant articles and documents

Preparation method of CDK4/6 kinase inhibitor SHR6390

The invention relates to a preparation method of a CDK4/6 kinase inhibitor SHR6390. According to the preparation method disclosed by the invention, the SHR6390 can be rapidly and effectively prepared through six steps of chemical reactions. In the first step of reaction, the advantage of high reaction activity of the fourth site of pyrimidine is fully utilized, a target product compound 3 can be well obtained under mild conditions, in the fourth step of reaction, after-treatment of the synthesis reaction of a compound 8 is simple, a good white solid product can be obtained basically through filtration and washing, purification is not needed, and the method is suitable for amplification and process 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.

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.

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 compound containing chlorobromopyrrole pyrimidinone structure

The invention provides a preparation method of a compound containing a chlorobromopyrrole pyrimidinone structure. The invention relates to the field of chemical synthesis, in particular to an industrial preparation method of a 6-bromo-2-chloro-8-cyclopentyl--5methyl-pyrido[2,3-d]pyrimidine-7(8H) ketone Palbociclib intermediate with a structure as shown in a formula (I) which is described in the specification. According to the method, a compound shown as a formula (II) is used as a raw material, reacts under the conditions of a specific bromination reagent and acid, and is treated by an aqueoussolution of a reducing inorganic salt to obtain a compound shown as a formula (I). Moreover, compared with a traditional process, the preparation method disclosed by the invention is simple and convenient to operate, high in product yield, high in product purity and suitable for industrial production, and has a great implementation value and social and economic benefits.

Preparation method of palbociclib parent nucleus structure compound

The invention provides a preparation method of a palbociclib mother nucleus structure compound. The preparation method comprises the following step: preparing the palbociclib parent nucleus structurecompound as shown in a formula (I) which is described in the specification by taking cytosine or an intermediate 1 or an intermediate 2 as a starting raw material, wherein the intermediate 1 and the intermediate 2 are as described in the specification, and X is selected from halogen. The method is wide in the source of the starting material, simple in operation process, less in side reaction and high in purity, and accords with the concept of modern green industrial production.

Preparation method of pyridine pyrimidine derivative

The invention discloses a preparation method of a pyridine pyrimidine derivative. The preparation method comprises following steps: 3-methyl-2-glutaconate diester and cyclopentamine are subjected to amidation condensation to prepare 1-cyclopentyl-4-methylpyridine-2, 6-(1H, 5H)-dione, and one-pot condensation with methylation reagent (N, N-dimethylformamide acetal) and urea is carried out so as toobtain 2-hydroxyl-5-methyl-8-cyclopentyl pyridine [2, 3-d] pyrimidine-8-hydro-7-one; and then chlorination and bromination reaction are carried out to prepare 2-chlor-5-methyl-6-bromo-8-cyclopentyl pyridine [2, 3-d] pyrimidine-8-hydro-7-one. The preparation method possesses following advantages: using of expensive trihalogen pyrimidine, palladium salt catalyst, and 3-borate substituted ethyl crotonate is avoided; the adopted raw materials are cheap and easily available; operation is convenient; reaction yield is stable; less three wastes are generated; reaction atom economical benefit is high;cost is low; and the preparation method is convenient for green industrialized production.

PYRIMIDINE OR PYRIDOPYRIDONE COMPOUND AND APPLICATION THEREOF

The present invention discloses a pyrimidine or pyridopyridone compound as shown in formula (I) and an application thereof relating to the technical field of medicament preparation. The compound can selectively suppress cyclin-dependent kinases (Cdks) CDK

Preparation method of Palbociclib intermediate

The invention relates to the field of medicine synthesis, and discloses a preparation method of a Palbociclib intermediate. In the preparation process, 5-bromine-2,4-dichloropyrimidine is used as a starting raw material; through ammoniation substitution reaction, green solvent PEG (polyethylene glycol) promotion palladium catalysis coupled reaction, BTC (triphosgene) promotion cyclization reactionand NBS (N-bromosuccinimide) bromination reaction, a target compound V is finally obtained; through aftertreatment improvement, the HPLC purity of the final product can reach 99 percent or higher. Compared with a traditional process, the preparation method has the main beneficial effects that the reaction conditions are mild; the operation is simple and convenient; the palladium catalyst consumption is low; the yield is high; the cost is low; the three-waste quantity is small; the industrialization is easy; high implementation values and socioeconomic benefits are realized.

Novel synthetic method of Palbociclib

The invention provides a novel synthetic method of Palbociclib, comprising the following steps: 1) under the action of alkali and a solvent, an intermediate V and an intermediate B1 undergo a condensation reaction to obtain a compound VI; 2) the compound VI undergoes exchange with a Grignard reagent, and then the exchange reaction product reacts with an acylation reagent to obtain a compound VII; when X is acetyl, the compound VI is the compound VII; 3) the compound VII undergoes deprotection reaction under the action of hydroxyethanesulphonic acid and finally salification is conducted so as to obtain the finished product Palbociclib X. the synthetic method has a simple process route, is low-cost, and is suitable for industrial production. The synthetic route is as shown in the specification.