65774-92-7

Upstream product

• 141-97-9 ethyl acetoacetate 
• 1572-10-7 3⁽⁵⁾-phenylpyrazol-5⁽³⁾-amine 
• 827-41-8 3-phenylpyrazol-5-amine 
• 4692-94-8 N-(1,3-benzothiazol-2-yl)-3-oxobutanamide 
• 614-16-4 Benzoylacetonitrile 

Downstream Products

• 65774-88-1 4,5-dimethyl-2-phenyl-4H-pyrazolo[1,5-a]pyrimidin-7-one 
• 65774-97-2 1,5-dimethyl-2-phenyl-1H-pyrazolo[1,5-a]pyrimidin-7-one 
• 77494-00-9 5-Methyl-2-phenyl-4H-pyrazolo[1,5-a]pyrimidine-7-thione 
• 77506-96-8 7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine 

Relevant academic research and scientific papers

β-Oxo anilides in Heterocyclic Synthesis: Novel synthesis of polyfunctionally pyridines, pyrimidines and benzothiazole derivatives

ACETOACETANILIDE the arylidine derivatives derivative 3 and 6a, 1 was b. The reacted Hantzsch with aromatic amides aldehydes 7a,b were 2 prepared to yield by the one-pot cyclization reaction of a mixture of 2 moles of 1, aqueous ammonia and aromatic aldehydes. Treatment of 1 with ethanol containing equivalent amount of piperidine or morpholine furnished the isolable products 8a and 8b. Compound 1 underwent interamolecular heterocyclization on boiling conc. sulfuric acid, afforded 9. Also, the reaction of compound 1 with hydroxylamine hydrochloride in ethanol and sodium acetate afforded the oxime derivative 10. Furthermore, reactions of compound 1 with o-aminothiophenol furnished 11. Reactions of 1 with arylidine derivatives give compounds 13 and 16a-d. Treatment of compound 16d with elemental sulfur afforded the thieno[3,4-c]pyridine derivative 18. Treatment of 16a with hydrazine hydrate in boiling ethanol afforded the pyrazolo[3,4-b]pyridine derivatives 19. Also, compound 16a was reacted with ethylchloroacetate giving 20. Compound 20 was cyclized into the corresponding thieno[2,3-b]-pyridine derivative 21 upon boiling with ethanol containing a few drops of sodium ethoxide solution. Furthermore, compound 1 readily reacted with cyanothioacetamide to yield compound 22. Fusion of compound 1 with malononitrile over melting point without solvent in presence of ammonium acetate or refluxing in ethanolic piperidine afforded the pyridone 23a. Also, the pyridone derivative 23b was obtained by reacting compound 1 with cyanoacetamide. The reaction of acetoacetanilide 1 with ω-bromoacetophenones afforded 28a,b. Treatment of 1 with benzoyl and ethoxy carbonyl isothiocyanates afforded the pyrimidine derivatives 30a,b. The reaction of 1 with aminopyrazole gave the pyrazolopyrimidine 33. Coupling of 1 with diazonium salt of compounds 34a,b yielding 37a,b.

Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation

A simple one-pot method for the microwave-assisted synthesis of substituted pyrazolo[1,5-a]pyrimidinones, a core scaffold in many bioactive and pharmaceutically relevant compounds, has been established. A variety of substituents was tolerated at the 2 and 5 positions, including functionalized aryls, heterocycles, and alkyl groups.

PYRAZOLOPYRIMIDINYL INHIBITORS OF UBIQUITIN-ACTIVATING ENZYME

Disclosed are chemical entities that inhibit ubiquitin-activating enzyme (UAE), each of which is a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein Y is and W, Z, XY, RY1, RY2 and RY3 are defined herein; pharmaceutical compositions comprising the chemical entities; and methods of using the chemical entities. These chemical entities are useful for treating disorders, particularly cell proliferation disorders, including cancers.

Condensation of 5-aminopyrazoles unsubstituted in position 1 with β-keto esters

Condensation of β-keto esters with 5-aminopyrazoles unsubstituted in position 1 gives 7-oxopyrazolo[1, 5-a]pyrimidines.