29274-23-5

Usage

Uses

Used in Pharmaceutical Industry:
4H-PYRAZOLO[1,5-A]PYRIMIDIN-7-ONE is used as a pharmaceutical intermediate for the development of various drugs. Its unique structure allows it to be a key component in the synthesis of therapeutic agents targeting specific biological pathways or receptors.
Used in Research and Development:
In the research field, 4H-PYRAZOLO[1,5-A]PYRIMIDIN-7-ONE serves as a valuable compound for studying the properties and mechanisms of pyrimidine derivatives. It can be utilized in the design and testing of new chemical entities, contributing to the advancement of scientific knowledge and potential drug discovery.
Used in Chemical Synthesis:
4H-PYRAZOLO[1,5-A]PYRIMIDIN-7-ONE is used as a building block in the synthesis of more complex organic molecules. Its versatile structure makes it suitable for further functionalization and incorporation into a wide range of chemical products, including specialty chemicals and materials for various applications.

InChI:InChI=1/C6H5N3O/c10-6-2-3-7-5-1-4-8-9(5)6/h1-4,7H

Upstream product

• 874-14-6 1,3-dimethyluracil 
• 1820-80-0 3-aminopyrazole 
• 1117-37-9 ethyl (E)-3-(dimethylamino)acrylate 
• 1225387-53-0 3⁽⁵⁾-aminopyrazole 
• 109-94-4 formic acid ethyl ester 
• 29274-18-8 ethyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate 
• 197367-75-2 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid 
• 141-78-6 ethyl acetate 

Downstream Products

• 877173-84-7 3-bromo-7-chloropyrazolo[1,5-a]pyrimidine 
• 1404086-53-8 (S)-N-(1-(5-Methoxy-3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)ethyl)pyrazolo[1,5-a]pyrimidin-7-amine 
• 58347-49-2 7-chloropyrazolo[1,5-a]pyrirnidine 

Relevant academic research and scientific papers

Novel Hinge-Binding Motifs for Janus Kinase 3 Inhibitors: A Comprehensive Structure-Activity Relationship Study on Tofacitinib Bioisosteres

The Janus kinases (JAKs) are a family of cytosolic tyrosine kinases crucially involved in cytokine signaling. JAKs have been demonstrated to be valid targets in the treatment of inflammatory and myeloproliferative disorders, and two inhibitors, tofacitinib and ruxolitinib, recently received their marketing authorization. Despite this success, selectivity within the JAK family remains a major issue. Both approved compounds share a common 7H-pyrrolo[2,3-d]pyrimidine hinge binding motif, and little is known about modifications tolerated at this heterocyclic core. In the current study, a library of tofacitinib bioisosteres was prepared and tested against JAK3. The compounds possessed the tofacitinib piperidinyl side chain, whereas the hinge binding motif was replaced by a variety of heterocycles mimicking its pharmacophore. In view of the promising expectations obtained from molecular modeling, most of the compounds proved to be poorly active. However, strategies for restoring activity within this series of novel chemotypes were discovered and crucial structure-activity relationships were deduced. The compounds presented may serve as starting point for developing novel JAK inhibitors and as a valuable training set for in silico models.

Regioselective synthesis of 1- and 4-substituted 7-oxopyrazolo[1,5-a]pyrimidine-3-carboxamides

The synthesis of 7-substituted pyrazolo[1,5-a]pyrimidine-3-carboxamides was studied. First, methyl 7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate (5) was prepared in three steps from methyl 5-amino-1H-pyrazole-4-carboxylate (3). Treatment of 5 with POCl3 gave the highly reactive 7-chloro derivative 10, which was reacted with amines, benzyl alcohol, and phenylboronic acid in the presence of Pd-catalyst to give the corresponding 7-substituted derivatives 11. Hydrolysis of the esters 5 and 11 followed by amidation gave the corresponding carboxamides 16a-h and 15. Regioselectivity of N-alkylation of 7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylic acid derivatives 5 and 16 was tunable by the carboxy function. Alkylation of the secondary amides 16a-f furnished the 1-alkyl derivatives 17a-f, whereas the ester 5 and the tertiary amides 16g,h gave the 4-alkyl derivatives 14a-d and 16m,n, selectively.

Synthesis of pyrazolo[1,5-α]pyrimidinone regioisomers

(Chemical Equation Presented) This work describes two distinct routes to prepare pyrazolo-[1,5-α]pyrimidin-7-ones and two distinct routes to prepare pyrazolo[1,5-α]pyrimidin-5-ones. Use of 1,3-dimethyluracil as the electrophile in the preparation of the p

Pyrazolopyrimidines as protein kinase inhibitors

In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a] pyrimidine compounds as inhibitors of protein and/or checkpoint kinases, methods of preparing such compounds, pharmaceutical compositions including one or more such compounds, methods of preparing pharmaceutical formulations including one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the protein or checkpoint kinases using such compounds or pharmaceutical compositions.

PYRAZOLO[1,5-A] PYRIMIDINE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

The present invention relates to certain pyrazolo[1,5-a]pyrimidine compounds, to processes for their preparation, compositions comprising them and methods of using them. The compounds are useful in the treatment of cancer. Novel screening methods are also

Studies with functionally substituted enamines: The reactivity of enaminals and enamino esters toward naphthoquinone, hydrazonoyl halides, aminoazoles and hippuric acid

Whereas enamines 1a,b react with naphthoquinone (2) to yield the naphthofuranals 5a,b, enamine ester 1c react with 2 to yield benzoindole derivatives 7. Enamine 1b reacts with hydrazonoyl halides 8 to yield 3,4-disubstituted pyrazoles 12. On the other hand, the enaminal 1a failed to react with 8, while enamine ester 1c afforded hydrazone 16 on treatment with 8. The enamino ester 1b afforded triethyl 1,3,5-benzenetricarboxylates on refluxing in acetic acid. Georg Thieme Verlag Stuttgart.

Preparation and pyrolysis of 1-(pyrazol-5-yl)-1,2,3-triazoles and related compounds

1-(Pyrazol-5-yl)-1,2,3-triazoles 8a, 9a and 10 are prepared by cycloaddition of 5-azidopyrazoles with methyl prop-2-ynoate. The regiochemistry of the process is confirmed by synthesis of 9a using an authentic route from ethyl 2-formyl-2-diazoacetate 13. Flash vacuum pyrolysis of 8a, 9a and 10 gives 5-methoxypyrazolo[1,5-a]pyrimidin-7-ones 16-18 by a mechanism involving an unexpected oxoketenimineimidoyl ketene rearrangement as the key step. The mechanism is supported by a 13C labelling experiment. A general route to pyrazolo[1,5-a]pyrimidin-7-ones from pyrazolylaminomethylene Meldrum's acid derivatives (e.g. 30-32) is also reported.