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

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
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CAS No. 571188-82-4
Cat. No. CS-B0335
Molecule weight584.51
Purity≥97%
MDL No.MFCD09834002

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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|CS-B0335

Structure of 571188-82-4

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General Information

CAS No. 571188-82-4
Cat. No. CS-B0335
Purity ≥97%
MDL No. MFCD09834002
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₇H₃₄BrN₇O₃
Molecular Weight 584.51
Synonym(s) Palbociclib-016 Palbociclib Intermediate 4
SMILES O=C1N(C2CCCC2)C3=NC(NC(N=C4)=CC=C4N5CCN(CC5)C(OC(C)(C)C)=O)=NC=C3C(C)=C1Br

Description

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 is a synthetically versatile intermediate featuring a brominated pyrido[2,3-d]pyrimidinone core paired with a piperazine linker and tert-butyl ester handle. This configuration enables efficient downstream derivatization in medicinal chemistry campaigns targeting kinase inhibitors and bioactive heterocycles. The molecule exhibits robust stability under standard conditions and facilitates modular assembly of complex scaffolds through orthogonal functional group manipulation.

Application

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 serves as a key intermediate in the synthesis of kinase-inhibiting scaffolds. The bromo group enables palladium-catalyzed cross-coupling reactions, while the piperazine moiety offers versatility for further functionalization. The tert-butyl carbamate provides stability and ease of purification, facilitating downstream deprotection and integration into complex heterocyclic architectures.

Synthesis

Route1
- 571188-81-3
- 571188-59-5
- ~37%
- In-stock
  
  571188-82-4
References
- Barvian, Mark; Booth, Richard John; Ouin III, John; Thomas Repine, Joseph; Sheehan, Derek J.; Toogood, Peter Laurence; Vanderwel, Scott Norman; Zhou, Hairong Patent: US2003/149001 A1, 2003 ; US 20030149001 A1
Route2
- In-stock
  
  775288-71-6
- ~%
- In-stock
  
  571188-82-4
References
- Toogood, Peter L.; Harvey, Patricia J.; Repine, Joseph T.; Sheehan, Derek J.; VanderWel, Scott N.; Zhou, Hairong; Keller, Paul R.; McNamara, Dennis J.; Sherry, Debra; Zhu, Tong; Brodfuehrer, Joanne; Choi, Chung; Barvian, Mark R.; Fry, David W. Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2388 - 2406
Route3
- In-stock
  
  571189-16-7
- ~%
- In-stock
  
  571188-82-4
References
- Toogood, Peter L.; Harvey, Patricia J.; Repine, Joseph T.; Sheehan, Derek J.; VanderWel, Scott N.; Zhou, Hairong; Keller, Paul R.; McNamara, Dennis J.; Sherry, Debra; Zhu, Tong; Brodfuehrer, Joanne; Choi, Chung; Barvian, Mark R.; Fry, David W. Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2388 - 2406

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 105.48
LogP 5.17322
H_Acceptors 9
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperazine compounds

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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

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