65143-08-0

Upstream product

• 62564-64-1 1-phenyl-1H-pyrazolo<3,4-d>pyrimidine 5-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 5334-48-5 4-chloro-1-(phenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 555-16-8 4-nitrobenzaldehdye 
• 123-11-5 4-methoxy-benzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 529-20-4 2-methylphenyl aldehyde 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 620-23-5 m-tolyl aldehyde 
• 151-50-8 potassium cyanide 
• 53645-79-7 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 21314-17-0 1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 98-03-3 thiophene-2-carbaldehyde 
• 110212-00-5 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carbonitrile 

Downstream Products

• 134440-72-5 8-(Diethylamino)-7-methyl-1-phenyl-1H-pyrazolo<3,4-b><1,5>diazocine-4-carbonitrile 

Relevant academic research and scientific papers

The one-pot conversion of pyrimidinone derivatives into substituted pyrimidines using diphenylphosphinic chloride under a mild condition

Pyrimidinone derivatives reacted with diphenylphosphinic chloride followed by addition of nucleophiles to afford substituted pyrimidine derivatives at a mild temperature (20-66°C).

Several approaches to cyanide ion-catalyzed synthesis of 4-aroyl-1-phenyl-1h-pyrazolo[3,4-d]pyrimidines

- 4-Aroyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidines (5) were formed in low yields by reaction of 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (4) with arenecarbaldehydes (3) in the presence of potassium cyanide. Similar reaction of 4-tosyl-1-phenyl-1H-pyra

Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate

Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2).In the reaction pathway, the cyanation proceeds through the formation of the su

PREPARATION OF HETEROARENECARBONITRILES BY REACTION OF HETEROARENE N-OXIDES WITH TRIMETHYLSILYL CYANIDE IN THE PRESENCE OF DBU

Several heteroarenecarbonitriles were prepared from the corresponding heteroarene N-oxides by treatment with trimethylsilylcyanide (TMSCN) in the presence of a base in tetrahydrofuran (THF). 1,8-Diazabicyclo-7-undecene (DBU) was found to be an effective base for the cyanation.

Studies on Pyrazolopyrimidine Derivatives. XV. Reactions Involving the Formation of the Anion of the Reissert Compound Derived form 1H-Pyrazolopyrimidine

The anion (A) of the Reissert compound (1, 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile) was found to react with electrophiles in two ways.One is nucleophilic attack of the anion A.The other is self-decomposition of the anion A.Thus, A underwent nucleophilic attack with aromatic and aliphatic aldehydes (4a-j), resulting in the formation of the corresponding α-aryl (or alkyl)-1-phenyl-1H-pyrazolopyrimidin-4-ylmethyl benzoates (6a-j) together with 1-phenyl-1H-pyrazolopyrimidine (2), the 4,4'-dimer (7) of 2, O-benzoylaroins (8a-d), and O-benzoylcyanohydrins (9e-j).Nucleophilic substitution took place in the reaction of A with 2,4-dinitrochlorobenzene (14a) and methyl iodide (14d), giving the 4-(2,4-dinitrophenyl) derivative (17a) of 2 and 5,7-dibenzoyl-4-methyl-1-phenyl-4-(1-phenyl-1H-pyrazolopyrimidin-4-yl)-4,5,6,7-tetrahydro-1H-pyrazolopyrimidine-6-carbonitrile (19), respectively.However, the anion A did not react with other aryl (or alkyl) halides (14b, c, e), ketones (11a, b), 2-alkenonitriles (21a, b), and dimethylacetylenedicarboxylate (22), and underwent the known self-decomposition, resulting in the formation of products such as 2, 7, the cyano derivative (18) of 2, and the ester 6a.Keywords - pyrazolopyrimidine; Reissert compound; aldehyde; aryl halide; nucleophilic attack; self-decomposition; pyrazolopyrimidinemethanol

Studies on Pyrazolopyrimidine Derivatives. XIV. Preparation and Reactions of 1-Phenyl-1H-pyrazolo-pyrimidine Reissert Compound

The Reissert reaction of 1-phenyl-1H-pyrazolopyrimidine (4) in anhydrous methylene chloride using benzoyl chloride, trimethylsilyl cyanide, and a catalytic amount of aluminium chloride gave the corresponding Reissert compound (3, 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile) in 95percent yield.The alkaline hydrolysis of 3 in methanol resulted in the formation of 4, benzoic acid (7), and the 4,4'-dimer (9) of (4).The acid hydrolysis in dimethyl sulfoxide and in methanol proceeded with ring fission to give 5-amino-α-benzamido-1-phenyl-1H-pyrazole-4-acetonitrile (13), the acetamide (14), and the acetate (15).Compound 3 reacted with sodium hydride in dimethylformamide to give 4, 9, 1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile (20), α,1-diphenyl-1H-pyrazolopyrimidin-4-ylmethyl benzoate (21), and O-benzoylmandelonitrile (22).In the present paper, we compare the chemical properties of 3 with those of the isoquinoline Reissert compound (1, 2-benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile).Keywords-pyrazolopyrimidine Reissert compound; preparation; chemical property; hydrolysis; pyrazoleacetonitrile; carbanion; rearrangement; pyrazolopyrimidinemethanol