733039-23-1

Basic information

• Product Name: 4-PyriMidinaMine, 5-broMo-N-cyclopentyl-2-(Methylthio)-
• Synonyms: 4-PyriMidinaMine, 5-broMo-N-cyclopentyl-2-(Methylthio)-;5-bromo-N-cyclopentyl-2-(methylthio)pyrimidin-4-amine
• CAS NO: 733039-23-1
• Molecular Formula: C₁₀H₁₄BrN₃S
• Molecular Weight: 288.20726
• Mol File: 733039-23-1.mol

Chemical Properties

• Boiling Point: 419.1°C at 760 mmHg
• Flash Point: 207.3°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 3.11E-07mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 4-PyriMidinaMine, 5-broMo-N-cyclopentyl-2-(Methylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PyriMidinaMine, 5-broMo-N-cyclopentyl-2-(Methylthio)-(733039-23-1)
• EPA Substance Registry System: 4-PyriMidinaMine, 5-broMo-N-cyclopentyl-2-(Methylthio)-(733039-23-1)

Safety Data

• Hazardous Substances Data: 733039-23-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H14BrN3S/c1-15-10-12-6-8(11)9(14-10)13-7-4-2-3-5-7/h6-7H,2-5H2,1H3,(H,12,13,14)

Upstream product

• 49844-90-8 4-Chloro-2-methylthiopyrimidine 
• 63810-78-6 4?chloro?5?bromo?2?(methylthio)pyrimidine 
• 1003-03-8 Cyclopentamine 
• 81560-03-4 2-methylsulfanyl-5-bromopyrimidin-4-one 
• 5751-20-2 2-Methylthiouracil 
• 733039-20-8 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 362656-23-3 8?cyclopentyl?5?methyl?2?(methylthio)pyrido[2,3?d]pyrimidin?7(8H)?one 
• 571188-81-3 6?bromo?8?cyclopentyl?5?methyl?2?(methylsulfinyl)pyrido[2,3?d]pyrimidin?7(8H)?one 
• 571190-30-2 PD 0332991 
• 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 
• 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 
• 733039-22-0 (5-bromo-2-methanesulfonilpyrimidin-4-yl)cyclopentylamine 

Relevant articles and documents

A new and efficient protocol for the synthesis of the key intermediate of palbociclib

A new and efficient synthesis of 6-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)-pyrido[2,3-d]pyrimidin-7(8H)-one, a key intermediate of Palbociclib, starting from thiouracil was described. This protocol involved methylation, nucleophilic substitution, bromination, nucleophilic substitution, Heck reaction, ring closure, oxidation, and bromination to afford a key intermediate of Palbociclib with approximately 35% overall yield. The advantages of this developed synthetic strategy included improved overall yield, inexpensive starting materials, and readily controllable and cleaner reaction conditions.

A new route for the synthesis of Palbociclib

Abstract: In this paper, a novel synthetic method for Palbociclib was reported. It was synthesized in eight steps from 2-(methylthio) pyrimidin-4-(3H)-one with approximately 10% overall yield. This protocol started material 2-(methylthio) pyrimidin-4-(3H)-one, involved nucleophilic substitution by thionyl chloride, bromination, nucleophilic substitution by cyclopentylamine, a one pot-two step method (Heck reaction, ring close sequence), oxidation and bromination, cross-coupling reaction, Heck reaction, aqueous workup to afford Palbociclib. This synthetic route used inexpensive raw material and reagents, involved readily controllable reaction conditions and reduced environmental hazards. Graphic abstract: Synthesis of Palbociclib, a small molecule CDK inhibitor, starting from 2-(methylthio) pyrimidin-4-(3H)-one by 8 steps reaction. This method afforded the Palbociclib in 10% yield. [Figure not available: see fulltext.].

A Palumbo vial preparation method of the key intermediate (by machine translation)

The invention discloses a Palumbo Xilin key intermediate 6 - bromo - 2 - methyl sulfonyl - 8 - cyclopentyl - 5 - methyl pyridine and (2, 3 - d) pyrimidine - 7 (8 H) - ketone. The method uses the thiourea pyrimidine as the starting material, by methylation, chloro, bromo synthesis of 5 - bromo - 4 - chloro - 2 - methylthio-pyrimidine, then with the cyclopentamine alkylation, with 2 - butenoic acid by the heck reaction, then the intramolecular acylation reaction for the synthesis of 2 - methylthio - 8 - cyclopentyl - 5 - methyl pyridine and (2, 3 - d) pyrimidine - 7 (8 H) - one, finally with the NBS reaction for the preparation of 6 - bromo - 2 - methyl sulfonyl - 8 - cyclopentyl - 5 - methyl pyridine and (2, 3 - d) pyrimidine - 7 (8 H) - one. The preparation process of the present invention short step, not using the dangerous process, simple and convenient operation, low cost of raw materials, to meet the using requirements of the people. (by machine translation)

2-AMINOPYRIDINE SUBSTITUTED HETEROCYCLES AS INHIBITORS OF CELLULAR PROLIFERATION

The present invention provides substituted 2-aminopyridines of formula (I), wherein R1, A1, W, X, and Y are as defined in the specification, useful in treating cell proliferative disorders. The novel compounds of the present invention are potent inhibitors of cyclin-dependent kinases 4 (Cdk4).