269055-04-1

Basic information

• Product Name: Benzonitrile, 4-[[5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-
• CAS NO: 269055-04-1
• Molecular Formula: C20H14BrN5O
• Molecular Weight: 420.268
• Mol File: 269055-04-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-[[5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-[[5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-(269055-04-1)
• EPA Substance Registry System: Benzonitrile, 4-[[5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-(269055-04-1)

Safety Data

• Hazardous Substances Data: 269055-04-1(Hazardous Substances Data)

Upstream product

• 872-50-4 1-methyl-pyrrolidin-2-one 
• 4198-90-7 3,5-dimethyl-4-hydroxybenzonitrile 
• 269055-72-3 4-[(5-bromo-4-chloro-2-pyrimidinyl)amino]benzonitrile 
• 189956-45-4 4-[(4-hydroxy-2-pyrimidinyl)amino]benzonitrile 
• 244768-32-9 4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile 
• 873-74-5 4-Aminobenzonitrile 
• 1039021-95-8 4-(5-bromo-2-chloro-pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile 

Downstream Products

• 269055-64-3 5-bromo-4-chloro-N-(2,4,6-trimethylphenyl)-2-pyrimidinamine 
• 269055-74-5 4-[(4,5-dichloro-2-pyrimidinyl)amino]benzonitrile 
• 269055-15-4 etravirine 
• 1616667-63-0 C₂₅H₂₂BrN₅O₃ 
• 373791-74-3 C₂₃H₂₀BrN₅O₂ 

Relevant articles and documents

Palladium-Catalyzed Cyanation of Arenediazonium Tetrafluoroborate Derivatives with 2-(Piperidin-1-yl)acetonitrile as the Cyano Source

The present study describes the one-pot palladium-catalyzed cyanation of commercially available aryldiazonium tetrafluoroborate derivatives with 2-(piperidin-1-yl)acetonitrile (an organic cyano reagent) under mild conditions. This process utilizes a Pd/(Me3Si)2 system and is applied to a wide scope of aromatic diazonium substrates to give the corresponding nitrile-containing products in moderate to high yields (59 92%). This methodology is employed for the preparation of etravirine, a drug used for the treatment of HIV, and for transformations of 1H-indole-2-carbonitrile into compounds that are used as a NMDA receptor antagonists and that have high potential against mutant HIV strains. The mechanism proposed for this Pd-catalyzed cyanation involves cyanide ions, as confirmed using indicator paper.

Synthesis and late-stage functionalization of complex molecules through C-H fluorination and nucleophilic aromatic substitution

We report the late-stage functionalization of multisubstituted pyridines and diazines at the position α to nitrogen. By this process, a series of functional groups and substituents bound to the ring through nitrogen, oxygen, sulfur, or carbon are installed. This functionalization is accomplished by a combination of fluorination and nucleophilic aromatic substitution of the installed fluoride. A diverse array of functionalities can be installed because of the mild reaction conditions revealed for nucleophilic aromatic substitutions (SNAr) of the 2-fluoroheteroarenes. An evaluation of the rates for substitution versus the rates for competitive processes provides a framework for planning this functionalization sequence. This process is illustrated by the modification of a series of medicinally important compounds, as well as the increase in efficiency of synthesis of several existing pharmaceuticals.

Prodrugs of hiv replication inhibiting pyrimidines

The present invention concerns compounds of formula (A1)(A2)N—R1 (I),the N-oxide forms, the pharmaceutically acceptable addition salts, the quaternary amines and stereochemically isomeric forms thereof, wherein R1 is substituted C1-6alkyl; —S(=O)—R8; —S(=O)2—R8; C7-12alkylcarbonyl; optionally substituted C1-6alkyloxycarbonylC1-6alkylcarbonyl; with R8 being C1-6alkyl, aryl1 or Het1; (A1)(A2)N— is the covalently bonded form of the corresponding intermediate of formula (A1)(A2)N—H, which is a HIV replication inhibiting pyrimidine of formula 1