1666-86-0

Basic information

• Product Name: Pyrimidine, 2,4,6-triphenyl-
• CAS NO: 1666-86-0
• Molecular Formula: C22H16N2
• Molecular Weight: 308.382
• Mol File: 1666-86-0.mol

Chemical Properties

• CAS DataBase Reference: Pyrimidine, 2,4,6-triphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimidine, 2,4,6-triphenyl-(1666-86-0)
• EPA Substance Registry System: Pyrimidine, 2,4,6-triphenyl-(1666-86-0)

Safety Data

• Hazardous Substances Data: 1666-86-0(Hazardous Substances Data)

Upstream product

• 29509-91-9 4-chloro-2,6-diphenyl-1,3-pyrimidine 
• 24737-87-9 1,3,5,6-tetraphenyl-1,4-dihydro-pyridazine 
• 100-47-0 benzonitrile 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 64-17-5 ethanol 
• 3274-61-1 2,4,5-triphenylpyrrole 
• 7664-41-7 ammonia 
• 591-50-4 iodobenzene 
• 1670-14-0 benzamidine monohydrochloride 
• 3764-01-0 2,4,6-trichloropyrimidine 
• 15421-92-8 N-benzylbenzamidine 
• 100-52-7 benzaldehyde 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 1207867-16-0 [OsH₂(P(iPr)3)2(2,4,6-triphenylpyrimidine(-2H))] 
• 1207867-17-1 [(OsH₂(P(iPr)3)2)2(2,4,6-triphenylpyrimidine(-4H))] 
• 580-35-8 2,4,6-triphenylpyridine 
• 57162-46-6 3-n-propyl-2,4,6-triphenylpyridine 
• 71722-06-0 6-methyl-2,4,6-triphenyl-1,6-dihydropyrimidine 
• 345942-77-0 6-n-butyl-2,4,6-triphenyl-1,6-dihydropyrimidine 

Relevant articles and documents

Base-Mediated Three-Component Tandem Reactions for the Synthesis of Multisubstituted Pyrimidines

A base-mediated three-component tandem reaction for the synthesis of multisubstituted pyrimidines from amidines, aryl alkynes, and aldehydes in a one-pot manner has been developed. Advantages of this transformation include being transition-metal-free, high efficiency, available starting materials, and being environmentally friendly.

Facile synthesis of triarylpyrimidines with microwave-irradiated reactions of N-phenacylpyridinium chloride

In a system of ammonium acetate and acetic acid under microwave irradiation, N-phenacylpyridinium chloride 1 reacted with 2 mol of aromatic aldehydes 2a-h to give 2,4,6-triarylpyrimidine 3a-h, reacted with pyridinecarboxaldehyde 4a-c and acetophenone 5 to yield bipyridine derivatives 6a-c. The structure of the products was characterized with 1H NMR, 13C NMR, IR, and mass spectroscopy. Copyright Taylor & Francis Group, LLC.

Oxidative Coupling with Zr(IV) Supported by a Noninnocent Anthracene-Based Ligand: Application to the Catalytic Cotrimerization of Alkynes and Nitriles to Pyrimidines

We report the synthesis and reactivity of Zr complexes supported by a 9,10-anthracenediyl-linked bisphenoxide ligand, L. ZrIVLBn2 (1) undergoes facile photolytic reduction with concomitant formation of bibenzyl and ZrIVL(THF)3 (2), which displays a two-electron reduced anthracene moiety. Leveraging ligand-stored reducing equivalents, 2 promotes the oxidative coupling of internal and terminal alkynes to isolable zirconacyclopentadiene complexes, demonstrating the reversible utilization of anthracene as a redox reservoir. With diphenylacetylene under CO, cyclopentadienone is formed stoichiometrically. 2 is competent for the catalytic formation of pyrimidines from alkynes and nitriles. Mechanistic studies suggest that selectivity for pyrimidine originates from preferred formation of an azazirconacyclopentadiene intermediate, which reacts preferentially with nitriles over alkynes.

Iron-Catalyzed Alkyne-Based Multicomponent Synthesis of Pyrimidines under Air

An iron-catalyzed sustainable, economically affordable, and eco-friendly synthetic protocol for the construction of various trisubstituted pyrimidines is described. A wide range of trisubstituted pyrimidines were prepared using a well-defined, easy to prepare, bench-stable, and phosphine-free iron catalyst featuring a redox-noninnocent tridentate arylazo pincer under comparatively mild aerobic conditions via dehydrogenative functionalization of alcohols with alkynes and amidines.

Metal-free cascade synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones

A convenient metal-free synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones has been developed. In this procedure, various structural 2-aminopyrimidines, as well as 4,5-dihydroisoxazol-5-ols and pyrazoles were synthesized in moderate to excellent yields. A plausible mechanism was also proposed for the cascade reaction. This method represents an effective strategy towards the synthesis of unsymmetrical 2-aminopyrimidines.

Flow reactor approach for the facile and continuous synthesis of efficient Pd@Pt core-shell nanoparticles for acceptorless dehydrogenative synthesis of pyrimidines from alcohols and amidines

Carbon supported Pd@Pt core-shell nanoparticles catalyst was prepared in a flow reactor toachieve enhanced catalytic activities with low Pt loading for the acceptorless dehydrogenative synthesis of pyrimidines. Spectroscopic (XAS analysis) and microscopic (HAADF-STEM) techniques reveled that the core-shell structure was formed by the applied preparation method. The Pd@Pt/PVP (polyvinylpyrrolidone)/C catalyst showed the activity for the three component one pot synthesis of pyrimidines through a series of consecutive reactions including oxidation of alcohols, C[sbnd]C, and C[sbnd]N coupling, followed by heterocyclization and dehydrogenation employing various primary alcohols, secondary alcohols, and amidines. The reaction mechanism on Pd@Pt/PVP/C catalyst was explored by comparison with the control experiments.

Bioinspired Radical-Mediated Transition-Metal-Free Synthesis of N-Heterocycles under Visible Light

A redox-active iminoquinone motif connected with π-delocalized pyrene core has been reported that can perform efficient two-electron oxidation of a class of substrates. The design of the molecule was inspired by the organic redox cofactor topaquinone (TPQ), which executes amine oxidation in the enzyme, copper amine oxidase. Easy oxidation of both primary and secondary alcohols happened in the presence of catalytic KOtBu, which could reduce the ligand backbone to its iminosemiquinonate form under photoinduced conditions. Moreover, this easy oxidation of alcohols under aerobic condition could be elegantly extended to multi-component, one-pot coupling for the synthesis of quinoline and pyrimidine. This organocatalytic approach is very mild (70 °C, 8 h) compared to a multitude of transition-metal catalysts that have been used to prepare these heterocycles. A detailed mechanistic study proves the intermediacy of the iminosemiquinonate-type radical and a critical hydrogen atom transfer step to be involved in the dehydrogenation reaction.

Method for catalytic preparation of medical intermediate 2,4,6-triarylpyrimidine derivative

The invention discloses a method for catalytically preparing a medical intermediate 2,4,6-triarylpyrimidine derivative, and belongs to the technical field of pharmaceutical chemicals. The method comprises the following steps: adding a reaction raw materia

Iron Nitrate-Mediated Selective Synthesis of 3-Acyl-1,2,4-oxadiazoles from Alkynes and Nitriles: The Dual Roles of Iron Nitrate

A direct strategy for the selective synthesis of 3-acyl-1,2,4-oxadiazoles from alkynes and nitriles has been developed under iron(III) nitrate-mediated conditions. The mechanism includes three sequential procedures: Iron(III) nitrate-mediated nitration of

Selective synthesis of pyrimidines from cinnamyl alcohols and amidines using the heterogeneous OMS-2 catalyst

Herein, an efficient aerobic oxidative synthesis of pyrimidines was carried out using cinnamyl alcohols and amidines catalyzed by manganese oxide octahedral molecular sieve (OMS-2). The heterogeneous catalytic method features base-/additive-free conditions, wide substrate scope, use of O2 as a green oxidant, and simple operation. Moreover, the OMS-2 catalyst prepared by the conventional reflux method demonstrates catalytic selectivity, activity, and excellent recyclability.