2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide

Base Information

• Chemical Name: 2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide
• CAS No.: 1421367-56-7
• Molecular Formula: C₂₄H₃₂N₆O₂
• Molecular Weight: 436.557
• Mol file: 1421367-56-7.mol

Synonyms:2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide

Chemical Property of 2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide

There total 8 articles about 2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C18H27N5O4S + benzylamine (100-46-9) → 2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide (1421367-56-7)

Guidance literature:

With triethylamine; In 1,4-dioxane; Reflux;

DOI:10.1016/j.bmcl.2012.12.013

Reference yield:

4-(cyclopentylamino)-2-(methylthio)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide (1421367-69-2) → 2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide (1421367-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C

2: triethylamine / 1,4-dioxane / Reflux

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.bmcl.2012.12.013

Reference yield:

4-chloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid (74840-34-9) → 2-(benzylamino)-4-(cyclopentylamino)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide (1421367-56-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 95 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / ethanol / 16 h / 90 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.1c00845

upstream raw materials:

4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride

C₁₃H₁₇ClN₄O₂S

4-(cyclopentylamino)-2-(methylthio)-N-(3-(2-oxopyrrolidin-1-yl)propyl)pyrimidine-5-carboxamide

benzylamine

Refernces

• 1、 Powell, Noel A.,Hoffman, Jennifer K.,Ciske, Fred L.,Kaufman, Michael D.,Kohrt, Jeffrey T.,Quin III, John,Sheehan, Derek J.,Delaney, Amy,Baxi, Sangita M.,Catana, Cornel,McConnell, Patrick,Ohren, Jeff,Perrin, Lisa A.,Edmunds, Jeremy J.. "Highly selective 2,4-diaminopyrimidine-5-carboxamide inhibitors of Sky kinase". . p. 1046 - 1050. Retrieved 2013/03/14.