tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate
• CAS No.: 866084-31-3
• Molecular Formula: C₃₃H₄₅N₇O₄
• Molecular Weight: 603.765
• Mol file: 866084-31-3.mol

Synonyms:tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate;Palbociclib INT;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;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-carboxylic acid tert-butyl ester;2-Methyl-2-propanyl 4-(6-{[8-cyclopentyl-5-methyl-7-oxo-6-(1-prop oxyvinyl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}-3-pyridin yl)-1-piperazinecarboxylate

Chemical Property of tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate

Chemical Property:

• Boiling Point: 764.2±70.0 °C(Predicted)
• PKA: 5.24±0.10(Predicted)
• PSA: 114.71000
• Density: 1.224±0.06 g/cm3(Predicted)
• LogP: 5.88390
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

tert-Butyl4-[6-[[6-(1-Butoxyethenyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl]amino]-pyridin-3-yl]-piperazine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl 4-[6-[[6-(1-Butoxyethenyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl]amino]-pyridin-3-yl]-piperazine-1-carboxylate is an intermediate in the commercial development of palbociclib, a highly selective reversible inhibitor of CDK 4/6 for breast cancer treatment.

Technology Process of tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)pyridin-3-yl)piperazine-1-carboxylate

There total 14 articles about tert-butyl 4-(6-(8-cyclopentyl-5-Methyl-7-oxo-6-(1-propoxyvinyl)-7,8-dihydropyrido[2,3-d]pyriMidin-2-ylaMino)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: 96.0%

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) + -butyl vinyl ether (111-34-2,92680-80-3) → 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 (866084-31-3)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; at 80 - 85 ℃; for 8h; Time;

Reference yield:

4-(6-nitropyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (571189-16-7) → 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 (866084-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 42 - 47 °C / 2585.81 Torr / Inert atmosphere

2: isopropylmagnesium chloride / tetrahydrofuran / 20 - 60 °C / Inert atmosphere

3: palladium diacetate; N-ethyl-N,N-diisopropylamine; bis[2-(diphenylphosphino)phenyl] ether / butan-1-ol / 2.5 h / 95 °C / Inert atmosphere

With 5%-palladium/activated carbon; hydrogen; isopropylmagnesium chloride; palladium diacetate; N-ethyl-N,N-diisopropylamine; bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; ethyl acetate; butan-1-ol;

Reference yield:

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) + -butyl vinyl ether (111-34-2,92680-80-3) → 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 (866084-31-3)

Guidance literature:

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; With isopropylmagnesium chloride; In tetrahydrofuran; at -5 - 10 ℃; Inert atmosphere;

-butyl vinyl ether; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 70 - 100 ℃; for 12h; Temperature; Inert atmosphere;

upstream raw materials:

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

-butyl vinyl ether

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

Cyclopentamine

Downstream raw materials:

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-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one isethionate

C₂₄H₂₉N₇O₂*2C₂H₆O₄S

Refernces

• 1、 -. "Preparation method and process of palbociclib". Paragraph 0039-0043. . Retrieved 2021/03/30.
• 2、 -. "Preparation method and product of palbociclib". Paragraph 0039; 0041; 0043; 0046. . Retrieved 2019/02/27.