91974-63-9

Basic information

• Product Name: 6-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• Synonyms: 6-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS NO: 91974-63-9
• Molecular Formula: C₁₂H₁₀N₄O
• Molecular Weight: 226.234
• Mol File: 91974-63-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(91974-63-9)
• EPA Substance Registry System: 6-methyl-1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(91974-63-9)

Safety Data

• Hazardous Substances Data: 91974-63-9(Hazardous Substances Data)

Upstream product

• 64257-07-4 5-amino-1,5-dihydro-6-methyl-1-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4-one 
• 100-63-0 phenylhydrazine 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 64-19-7 acetic acid 
• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 78-39-7 Triethyl orthoacetate 
• 1190204-68-2 ethyl (1-phenyl-4-oxopyrazolo[3,4-d]pyrimidin-6-yl)methylmercaptoacetate 
• 16078-71-0 ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate 
• 51649-80-0 5-amino-1-phenyl-1H-pyrazole-4-carboxylic acid 
• 51649-70-8 6-methyl-1-phenyl-1H-pyrazolo<3,4-d><1,3>oxazin-4(3H)-one 
• 141-78-6 ethyl acetate 

Downstream Products

• 107518-86-5 N-(furan-2-ylmethyl)-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1383659-09-3 6-methyl-4-(morpholin-4-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 101734-96-7 6-methyl-N,1-diphenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 132648-78-3 N,N-diethyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 5401-50-3 N-benzyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 5346-47-4 N-ethyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 459135-75-2 N-(2-methoxyphenyl)-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 23121-14-4 4-chloro-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 1383659-07-1 N-propyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 100974-14-9 N-isopropyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1383659-08-2 N-butyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 

Relevant articles and documents

Design and synthesis of pyrazolo[3,4-d]pyrimidines: Nitric oxide releasing compounds targeting hepatocellular carcinoma

A new series of pyrazolo[3,4-d]pyrimidines tethered with nitric oxide (NO) producing functionality was designed and synthesized. Sulforhodamine B (SRB) protein assay revealed that NO releasing moiety in the synthesized compounds significantly decreased the cell growth more than the des-NO analogues. Compounds 7C and 7G possessing N-para-substituted phenyl group, released the highest NO concentration of 4.6% and 4.7% respectively. Anti-proliferative activity of synthesized compounds on HepG2 cell line identified compounds 7h, 7p, 14a and 14b as the most cytotoxic compounds in the series of IC50?=?3, 5, 3 and 5?μM, respectively, compared to erlotinib as a reference drug (IC50?=?25?μM). Flow cytometry studies revealed that 7?h arrested the cells in G0/G1 phase of cell cycle while 7p arrested the cells in S phase. Moreover, docking study of the synthesized compounds on EGFR (PDB code: 1M17) and cytotoxicity study indicated that N-1 phenyl para substitution, pyrazole C-3 alkyl substitution and tethering the nitrate moiety through butyl group had a significant impact on the activity.

Montmorillonite K10 as an efficient and reusable catalyst for the synthesis of substituted pyrazolo[3,4-d]pyrimidin-4-ones under solvent-free conditions

A green and efficient method for the synthesis of pyrazolo[3,4-d]pyrimidin- 4-ones through heterocyclization reaction of 5-amino-1-phenyl-1H-pyrazole-4- carboxamides with orthoesters using Montmorillonite K10, as an effective and reusable catalyst, under solventfree conditions is described. The present methodology offers several advantages, such as a simple procedure with an easy work-up, short reaction times, high yields and the absence of any volatile and hazardous organic solvents. Furthermore, the products could be separated simply from the catalyst and the catalyst could be recycled and reused with only slight reduction in its catalytic activity.

Synthesis of some pyridothienopyrazolopyrimidopyrimidine and mercaptomethylpyrazolopyrimidine derivatives

Mercaptomethylpyrazolopyrimidine (2) was synthesized and reacted with ethyl chloroacetate to afford ethyl pyrazolpyrimidinylmethylmercapto acetate (3), which in turn was converted into the corresponding carbohydrazide 4. Carbohydrazide 4 reacts with a var