1001201-61-1

Basic information

• Product Name: tert-butyl 4-((5R,7S)-7-hydroxy-5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate
• Synonyms: tert-butyl 4-((5R,7S)-7-hydroxy-5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate;tert-butyl (5R,7R)-6,7-dihydro-7-hydroxy-5-Methyl-5H-cyclopenta[d]pyriMidin-4-ylcarbaMate;4-[(5R,7S)-6,7-Dihydro-7-hydroxy-5-methyl-5H-cyclopentapyrimidin-4-yl]-1-piperazinecarboxylic acid 1,1-dimethylethyl ester
• CAS NO: 1001201-61-1
• Molecular Formula: C₁₇H₂₆N₄O₃
• Molecular Weight: 334.41334
• Mol File: 1001201-61-1.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: tert-butyl 4-((5R,7S)-7-hydroxy-5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-((5R,7S)-7-hydroxy-5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate(1001201-61-1)
• EPA Substance Registry System: tert-butyl 4-((5R,7S)-7-hydroxy-5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate(1001201-61-1)

Safety Data

• Hazardous Substances Data: 1001201-61-1(Hazardous Substances Data)

Usage

General Description

Tert-butyl 4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate is a chemical compound that is used in medicinal chemistry research as a potential drug candidate. It is a piperazine derivative with a cyclopenta[d]pyrimidine moiety, and its tert-butyl ester group provides stability and enhances its pharmacokinetic properties. The compound has shown potential for therapeutic applications in the treatment of various diseases, particularly in the modulation of biological pathways associated with the targeted receptor. Further research and development efforts are underway to explore its pharmacological properties and evaluate its potential for clinical use.

Upstream product

• 1001178-85-3 (R)-2-mercapto-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol 
• 863725-39-7 (R)-pulegone dibromide 
• 65844-74-8 2-methylpropan-1,1,3-tricarboxylic acid trimethyl ester 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 1001180-18-2 tert-butyl 4-((5R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-piperazine-1-carboxylate 
• 1001180-15-9 tert-butyl 4-((5R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-piperazine-1-carboxylate 
• 1001180-40-0 (R)-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidine 1-oxide 
• 1001178-90-0 (R)-tert-butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate 

Downstream Products

• 1001180-49-9 tert-butyl 4-((5R,7S)-5-methyl-7-((4-nitrobenzoyl)oxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-piperazine-1-carboxylate 

Relevant articles and documents

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Herein, the route scouting and early process development of a key cyclopentylpyrimidine ketone intermediate toward the synthesis of Akt inhibitor Ipatasertib are described. Initial supplies of the intermediate were prepared through a method that commenced with the natural product (R)-(+)-pulegone and relied on the early construction of a methyl-substituted cyclopentyl ring system. The first process chemistry route, detailed herein, enabled the synthesis of the ketone on a hundred-gram scale, but it was not feasible for the requisite production of multikilogram quantities of this compound and necessitated the exploration of alternative strategies. Several new synthetic approaches were investigated towards the preparation of the cyclopentylpyrimidine ketone, in either racemic or chiral form, which resulted in the discovery of a more practical route that hinged on the initial preparation of a highly substituted dihydroxypyrimidine compound. The cyclopentane ring in the target was then constructed through a key carbonylative esterification and subsequent tandem Dieckmann cyclization-decarboxylation sequence that was demonstrated in a racemic synthesis. This proof-of-concept was later developed into an asymmetric synthesis of the cyclopentylpyrimidine ketone, which will be described in a subsequent paper, along with the synthesis of Ipatasertib.

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