5-Bromo-2-chloro-N-cyclopentylpyrimidin-4-amine

Name: 5-Bromo-2-chloro-N-cyclopentylpyrimidin-4-amine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 733039-20-8
Cat. No. CS-B0327
Purity≥97%
MDL No.MFCD13181206

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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5-Bromo-2-chloro-N-cyclopentylpyrimidin-4-amine|CS-B0327

Structure of 733039-20-8

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General Information

CAS No. 733039-20-8
Cat. No. CS-B0327
Purity ≥97%
MDL No. MFCD13181206
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₁BrClN₃
Molecular Weight 276.56
Synonym(s) 5-bromo-2-chloro-N-cyclopentyl-pyrimidin-4-amine
SMILES BrC1=CN=C(Cl)N=C1NC2CCCC2

Description

5-Bromo-2-chloro-N-cyclopentylpyrimidin-4-amine features a sterically hindered cyclopentyl group attached to the pyrimidine nitrogen, enhancing metabolic stability. The electron-deficient pyrimidine core supports efficient coupling in cross-coupling reactions. This bench-stable derivative enables rapid access to functionalized heterocycles in medicinal chemistry and materials synthesis.

Application

5-Bromo-2-chloro-N-cyclopentylpyrimidin-4-amine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its dual halogen functionality. The bromo and chloro groups offer orthogonal reactivity for sequential functionalization, while the N-cyclopentyl substituent enhances solubility and modulates electronic properties. Bench-stable and compatible with standard reaction conditions, it facilitates efficient synthesis of complex pyrimidine-based scaffolds used in kinase inhibitor development and other pharmaceutical applications.

Synthesis

Route1
- In-stock
  
  36082-50-5
- 1003-03-8
- ~99%
- In-stock
  
  733039-20-8
References
- Li, Zhihong; Wang, Xianghong; Eksterowicz, John; Gribble, Michael W.; Alba, Grace Q.; Ayres, Merrill; Carlson, Timothy J.; Chen, Ada; Chen, Xiaoqi; Cho, Robert; Connors, Richard V.; Degraffenreid, Michael; Deignan, Jeffrey T.; Duquette, Jason; Fan, Pingchen; Fisher, Benjamin; Fu, Jiasheng; Huard, Justin N.; Kaizerman, Jacob; Keegan, Kathleen S.; Li, Cong; Li, Kexue; Li, Yunxiao; Liang, Lingming; Liu, Wen; Lively, Sarah E.; Lo, Mei-Chu; Ma, Ji; McMinn, Dustin L.; Mihalic, Jeffrey T.; Modi, Kriti; Ngo, Rachel; Pattabiraman, Kanaka; Piper, Derek E.; Queva, Christophe; Ragains, Mark L.; Suchomel, Julia; Thibault, Steve; Walker, Nigel; Wang, Xiaodong; Wang, Zhulun; Wanska, Malgorzata; Wehn, Paul M.; Weidner, Margaret F.; Zhang, Alex J.; Zhao, Xiaoning; Kamb, Alexander; Wickramasinghe, Dineli; Dai, Kang; McGee, Lawrence R.; Medina, Julio C. Journal of Medicinal Chemistry, 2014 , vol. 57, # 8 p. 3430 - 3449

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 37.81
LogP 3.247
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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5-Bromo-2-chloro-N-cyclopentylpyrimidin-4-amine

CAS No. 733039-20-8

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