478554-41-5

Basic information

• Product Name: N-(4-pyrimidyl)triphenyliminophosphorane
• Synonyms: N-(4-pyrimidyl)triphenyliminophosphorane
• CAS NO: 478554-41-5
• Molecular Weight: 355.379
• Mol File: 478554-41-5.mol

Chemical Properties

• CAS DataBase Reference: N-(4-pyrimidyl)triphenyliminophosphorane(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-pyrimidyl)triphenyliminophosphorane(478554-41-5)
• EPA Substance Registry System: N-(4-pyrimidyl)triphenyliminophosphorane(478554-41-5)

Safety Data

• Hazardous Substances Data: 478554-41-5(Hazardous Substances Data)

Upstream product

• 163133-86-6 pyrimidin-4-amine 
• 1034-39-5 dibromotriphenylphosphorane 
• 603-35-0 triphenylphosphine 

Relevant articles and documents

Reaction between triphenylphosphine and aromatic amines in the presence of diethyl azodicarboxylate: An efficient synthesis of aryliminophosphoranes under neutral and mild conditions

An efficient synthesis of aryliminophosphoranes is described. A mixture of an aromatic amine, diethyl azodicarboxylate and triphenylphosphine undergo a Mitsonobu type reaction at ambient temperature in dry dichloromethane to afford aryliminophosphoranes in excellent yields.

Thermolysis of benzannulated enyne-carbodiimides. Application in the synthesis of pyrido[1′,2′:1,2]pyrimido[4,5-b]indoles and related heteroaromatic compounds

Several derivatives of the pyrido[1′,2′:1,2]pyrimido[4,5-b]indoles 4 and the pyrazino[1′,2′:1,2]-pyrimido[4,5-b]indoles 14 were synthesized by treatment of the benzannulated enyne-isocyanates 8 with the iminophosphoranes 9 and 13, respectively, for the aza-Wittig reaction followed by thermolysis. The reaction presumably proceeds through an initial formation of the corresponding benzannulated enyne-carbodiimides, such as 10, followed by a formal intramolecular hetero Diels-Alder reaction. Surprisingly, when the iminophosphorane 17 was used for condensation with 8, the expected pyrimido[1′,6′:1,2]pyrimido[4,5-b]indoles 16 were not obtained. Instead, the isomeric pyrimido[6′,1′:2,3]pyrimido[4,5-b]indoles 21 were isolated. Presumably, an alternative reaction pathway involving an initial [2 + 2] cycloaddition reaction to form 19 followed by ring opening could lead to 20 and, after an intramolecular radical-radical coupling, 21. Treatment of the urea derivatives 24 with dibromotriphenylphosphorane also produced in situ the benzannulated enynecarbodiimides 25, which on thermolysis gave the isoquinolino[2′,1′:1,2]pyrimido[4,5-b]indoles 26. Methylation of 4a, 14a, and 26a with methyl iodide occurred exclusively at the site of the indolo nitrogen. The planar geometry of those novel heteroaromatic compounds, resembling many DNA-binding agents, makes them potential candidates as DNA intercalators.