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

Base Information

• Chemical Name: 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
• CAS No.: 571188-82-4
• Molecular Formula: C27H34BrN7O3
• Molecular Weight: 584.516
• DSSTox Substance ID: DTXSID20457133
• Wikidata: Q82279861
• Mol file: 571188-82-4.mol

Synonyms: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;4-[6-(6-Bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester;tert-butyl 4-[6-[(6-bromo-8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]pyridin-3-yl]piperazine-1-carboxylate;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;CID 11157536;SCHEMBL2074567;DTXSID20457133;AMY14884;BCP11774;CS-B0335;WXA18882;MFCD09834002;1-Piperazinecarboxylic acid, 4-[6-[(6-bromo-8-cyclopentyl-7,8-dihydro-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]-3-pyridinyl]-, 1,1-dimethylethyl ester;AC-29046;DS-18869;FT-0697069;A869756;1-Piperazinecarboxylic acid,4-[6-[(6-bromo-8-cyclopentyl-7,8-dihydro-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]-3-pyridinyl]-,1,1-dimethylethyl ester;4-(6-(6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)pyridin-3-yl)piperazine-1-carboxylic acid tert-butyl ester;4-[6-(6-Bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-carboxylic acid tert-butyl ester;4-[6-[(6-Bromo-8-cyclopentyl-7,8-dihydro-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]-3-pyridinyl]-1-piperazinecarboxylic acid 1,1-dimethylethyl ester;t-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;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-carbox ylate;tert-butyl4-(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

Chemical Property of 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

Chemical Property:

• Vapor Pressure: 1.39E-20mmHg at 25°C
• Melting Point: >250℃
• Boiling Point: 720°C at 760 mmHg
• PKA: 5.24±0.10(Predicted)
• Flash Point: 389.3°C
• PSA: 105.48000
• Density: 1.439g/cm³
• LogP: 5.24910
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 583.19065
• Heavy Atom Count: 38
• Complexity: 911

Purity/Quality:

99% ^*data from raw suppliers

6-Desacetyl-6-bromo-N-BocPalbociclib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)N(C2=NC(=NC=C12)NC3=NC=C(C=C3)N4CCN(CC4)C(=O)OC(C)(C)C)C5CCCC5)Br
• Uses: 6-Desacetyl-6-bromo-N-Boc Palbociclib is an impurity of Palbociclib,(also known as compound number PD-0332991) is an experimental drug for the treatment of breast cancer being developed by Pfizer. It is a selective inhibitor of the cyclin-dependent kinases CDK4 and CDK6. Also, it is derived from 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one (B682195), which is used to prepare pyridino[2,3-d]pyrimidin-7(8H)-one derivatives as CDK4 and/or CDK6 inhibitors useful in the treatment of diseases. 6-Desacetyl-6-bromo-N-Boc Palbociclib is an impurity of Palbociclib (P139900),(also known as compound number PD-0332991) is an experimental drug for the treatment of breast cancer being developed by Pfizer. It is a selective inhibitor of the cyclin-dependent kinases CDK4 and CDK6.Also, it is derived from 6-Bromo-2-chloro-8-cyclopentyl-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one (B682195), which is used to prepare pyridino[2,3-d]pyrimidin-7(8H)-one derivatives as CDK4 and/or CDK6 inhibitors useful in the treatment of diseases.

Technology Process of 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

There total 26 articles about 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 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: 99.9%

tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (571188-59-5) + 2-chloro-5-methyl-6-bromo-8-cyclopentylpyridine[2,3-d]pyrimidin-8-hydro-7-one (1016636-76-2) → 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 (571188-82-4)

Guidance literature:

tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate; With isopropyl chloride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Large scale;

2-chloro-5-methyl-6-bromo-8-cyclopentylpyridine[2,3-d]pyrimidin-8-hydro-7-one; With isopropylmagnesium chloride; In tetrahydrofuran; at 70 ℃; Temperature; Large scale;

Reference yield: 92.0%

2-chloro-5-methyl-6-bromo-8-cyclopentylpyridine[2,3-d]pyrimidin-8-hydro-7-one (1016636-76-2) → 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 (571188-82-4)

Guidance literature:

tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; for 0.166667h;

2-chloro-5-methyl-6-bromo-8-cyclopentylpyridine[2,3-d]pyrimidin-8-hydro-7-one; In tetrahydrofuran; toluene; for 0.5h; Product distribution / selectivity;

Reference yield: 38.0%

6?bromo?8?cyclopentyl?5?methyl?2?(methylsulfinyl)pyrido[2,3?d]pyrimidin?7(8H)?one (571188-81-3) + tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (571188-59-5) → 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 (571188-82-4)

Guidance literature:

In toluene; for 7h; Heating;

DOI:10.1021/jm049354h

upstream raw materials:

6?bromo?8?cyclopentyl?5?methyl?2?(methylsulfinyl)pyrido[2,3?d]pyrimidin?7(8H)?one

tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

2-chloro-5-methyl-6-bromo-8-cyclopentylpyridine[2,3-d]pyrimidin-8-hydro-7-one

1-(6-nitropyridin-3-yl)piperazine

Downstream raw materials:

4-{6-[8-cyclopentyl-6-(1-ethoxyvinyl)-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino]pyridin-3-yl}piperazine-1-carboxylic acid tert-butyl ester

PD 0332991

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

6-acetyl-8-cyclopentyl-5-methyl-2-{[5-(piperazin-1-yl)pyridin-2yl]amino}pyrido[2,3-d]pyrimidin-7(8H)-one hydrochloride

Refernces

• 1、 -. "Preparation method and process of palbociclib". Paragraph 0034-0038. . Retrieved 2021/03/30.
• 2、 -. "Method for synthesizing palbociclib". Paragraph 0014; 0021-0022. . Retrieved 2019/07/11.