Imidazo[1,2-a]pyrimidin-7-amine

Name: Imidazo[1,2-a]pyrimidin-7-amine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 462651-80-5
Cat. No. CS-0094347
Purity≥95%
MDL No.None

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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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Imidazo[1,2-a]pyrimidin-7-amine|CS-0094347

Structure of 462651-80-5

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General Information

CAS No. 462651-80-5
Cat. No. CS-0094347
Purity ≥95%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₆N₄
Molecular Weight 134.14
Synonym(s) Imidazo[1,2-a]pyrimidin-7-amine (9CI) ISO 9001：2015 REACH
SMILES NC1=NC2=NC=CN2C=C1

Description

Imidazo[1,2-a]pyrimidin-7-amine serves as a privileged heterocyclic scaffold in medicinal chemistry, featuring a fused imidazole-pyrimidine core with a primary amine at the C7 position. This structural motif enables direct incorporation into kinase inhibitors and targeted therapeutics, offering enhanced binding affinity through hydrogen bonding and π-stacking interactions. The compound exhibits favorable solubility and stability under standard bench conditions, facilitating efficient downstream derivatization in drug discovery campaigns.

Application

Imidazo[1,2-a]pyrimidin-7-amine serves as a versatile heterocyclic scaffold in medicinal chemistry, enabling efficient construction of biologically active compounds. Its nitrogen-rich core exhibits favorable hydrogen-bonding capacity and metabolic stability, facilitating interactions with target proteins. The amine functionality allows for straightforward derivatization via acylation, alkylation, or coupling reactions, supporting rapid SAR exploration. Bench-stable and compatible with common reaction conditions, it functions as a key building block in the synthesis of kinase inhibitors and CNS-targeted therapeutics.

Synthesis

Route1
- 107-20-0
- In-stock
  
  156-81-0
- ~25%
- In-stock
  
  462651-80-5
- 1415729-03-1
References
- Tichenor, Mark S.; Keith, John M.; Jones, William M.; Pierce, Joan M.; Merit, Jeff; Hawryluk, Natalie; Seierstad, Mark; Palmer, James A.; Webb, Michael; Karbarz, Mark J.; Wilson, Sandy J.; Wennerholm, Michelle L.; Woestenborghs, Filip; Beerens, Dominiek; Luo, Lin; Brown, Sean M.; Boeck, Marlies De; Chaplan, Sandra R.; Breitenbucher, J. Guy Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 24 p. 7357 - 7362

Safety Information

Download SDS

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

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Computational Chemistry Data

TPSA 56.21
LogP 0.3115
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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Imidazo[1,2-a]pyrimidin-7-amine

CAS No. 462651-80-5

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