515880-87-2

Basic information

• Product Name: 4-[3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenol
• Synonyms: 4-[3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenol
• CAS NO: 515880-87-2
• Molecular Formula: C₁₇H₁₂N₄O
• Molecular Weight: 288.30338
• Mol File: 515880-87-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-[3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenol(515880-87-2)
• EPA Substance Registry System: 4-[3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenol(515880-87-2)

Safety Data

• Hazardous Substances Data: 515880-87-2(Hazardous Substances Data)

Upstream product

• 65192-28-1 2-(4-methoxyphenyl)malondialdehyde 
• 100-09-4 4-methoxybenzoic acid 
• 10445-91-7 4-(Chloromethyl)pyridine 
• 13121-99-8 pyridin-4-ylacetonitrile 
• 103851-89-4 3-(dimethylamino)-2-(4-pyridyl)prop-2-enenitrile 
• 92333-25-0 pyridin-4-ylacetonitrile hydrochloride 
• 216661-87-9 4-(4-pyridyl)-1H-pyrazol-3-amine 
• 216661-83-5 3-(bromo)-6-(4-methoxyphenyl)-pyrazolo(1,5-A)pyrimidine 
• 945376-95-4 4-(3-bromopyrazolo[1,5-a]pyrimidin-6-yl)phenol 
• 216661-87-9 5-amino-4-(pyridin-4-yl)-1H-pyrazole 
• 53868-40-9 2-(4-methoxyphenyl)-3-malonaldehyde 
• 216661-58-4 3-(pyridin-4-yl)-6-(4-methoxyphenyl)-pyrazolo(1,5-A)pyrimidine 

Downstream Products

• 597544-21-3 4-(2-(4-(3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)phenoxy)ethyl)morpholine 
• 1450754-58-1 6-(4-(2-(3-(but-3-ynyl)-3H-diazirin-3-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine 
• 1062368-41-5 6-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}-3-pyridin-4-yl-pyrazolo[1,5-a]pyrimidine 
• 866405-64-3 dorsomorphin 

Relevant articles and documents

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Microwave-assisted protocols for the expedited synthesis of pyrazolo[1,5-a] and [3,4-d]pyrimidines

General, high-yielding MAOS protocols for the expedited synthesis of functionalized pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-b]pyrimidines, as well as their pyrazole precursors, are described amenable to an iterative analogue library synthesis strategy for lead optimization.

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We have introduced solubilizing functionality to a 3,6-disubstituted pyrazolo[1,5-a]pyrimidine series of KDR kinase inhibitors to improve the physical properties of these compounds. The addition of a basic side-chain to the 6-aryl ring, introduction of 3-pyridyl groups, and most significantly, incorporation of a 4-pyridinonyl substituent at the 6-position of the core are modifications that maintain and often enhance the intrinsic potency of this class of inhibitors. Moreover, the improvements in physical properties result in marked increases in cellular activity and more favorable pharmacokinetics in rats. The synthesis and SAR of these compounds are described.