5,7-Dichloropyrazolo[1,5-a]pyrimidine

Name: 5,7-Dichloropyrazolo[1,5-a]pyrimidine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 57489-77-7
Cat. No. CS-W003486
Purity≥97%
MDL No.MFCD08273918

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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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5,7-Dichloropyrazolo[1,5-a]pyrimidine|CS-W003486

Structure of 57489-77-7

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General Information

CAS No. 57489-77-7
Cat. No. CS-W003486
Purity ≥97%
MDL No. MFCD08273918
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₃Cl₂N₃
Molecular Weight 188.01
Synonym(s) None
SMILES ClC1=CC(Cl)=NC2=CC=NN21

Description

5,7-Dichloropyrazolo[1,5-a]pyrimidine is a bench-stable heterocyclic scaffold featuring two chlorine substituents at electron-rich positions, enabling direct functionalization in cross-coupling reactions. This rigid, planar core integrates readily into kinase inhibitors and pharmaceutical intermediates, offering enhanced metabolic stability and predictable binding geometry in drug discovery applications.

Application

5,7-Dichloropyrazolo[1,5-a]pyrimidine serves as a versatile building block in medicinal chemistry, enabling efficient construction of biologically active heterocycles. The dichloro substitution pattern provides orthogonal reactivity for palladium-catalyzed cross-coupling and nucleophilic aromatic substitution, facilitating rapid diversification. Its bench-stable crystalline form simplifies handling and purification, while the fused pyrazolopyrimidine core offers favorable electronic properties for target engagement in kinase inhibitors and other pharmaceutical scaffolds.

Synthesis

Route1
- In-stock
  
  57489-70-0
- ~64%
- In-stock
  
  57489-77-7
References
- SCHERING CORPORATION; MENG, Zhaoyang; REDDY, Panduranga Adulla, P.; SIDDIQUI, M. Arshad; MANDAL, Amit, K.; LIU, Duan; ZHAO, Lianyun; MCRINER, Andrew Patent: WO2012/27234 A1, 2012 ; Location in patent: Page/Page column 40 ; WO 2012/027234 A1
Route2
- In-stock
  
  1820-80-0
- 105-53-3
- ~31%
- In-stock
  
  57489-77-7
References
- Kosugi, Tomomi; Mitchell, Dale R.; Fujino, Aiko; Imai, Minoru; Kambe, Mika; Kobayashi, Shinji; Makino, Hiroaki; Matsueda, Yohei; Oue, Yasuhiro; Komatsu, Kanji; Imaizumi, Keiichiro; Sakai, Yuri; Sugiura, Satoshi; Takenouchi, Osami; Unoki, Gen; Yamakoshi, Yuko; Cunliffe, Vicky; Frearson, Julie; Gordon, Richard; John Harris; Kalloo-Hosein, Heidi; Le, Joelle; Patel, Gita; Simpson, Donald J.; Sherborne, Brad; Thomas, Peter S.; Suzuki, Naotaka; Takimoto-Kamimura, Midori; Kataoka, Ken-Ichiro Journal of Medicinal Chemistry, 2012 , vol. 55, # 15 p. 6700 - 6715

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 30.19
LogP 2.0361
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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5,7-Dichloropyrazolo[1,5-a]pyrimidine

CAS No. 57489-77-7

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