403612-89-5

Usage

Class of organic compounds

quinazoline derivative (contains a benzene ring fused to a pyrimidine ring)

Unique chemical and physical properties

presence of a tert-butyl group and a chlorine atom

Uses

organic synthesis and medicinal chemistry (building block for the preparation of biologically active compounds)

Potential applications

pharmaceutical research and drug development

Industrial uses

production of specialty chemicals and fine organic synthesis

Upstream product

• 1885-29-6 anthranilic acid nitrile 
• 3282-30-2 pivaloyl chloride 
• 81102-88-7 N-(2-cyanophenyl)pivalamide 
• 118-92-3 anthranilic acid 
• 630-18-2 tert-butyl isocyanide 
• 13182-65-5 2-(tert-butyl)quinazolin-4(3H)-one 

Downstream Products

• 1256556-22-5 2-tert-butyl-4-morpholinoquinazoline 

Relevant academic research and scientific papers

Convenient and practical one-pot synthesis of 4-chloropyrimidines via a novel chloroimidate annulation

Reaction of aromatic or heteroaromatic 2-acyl(amino)nitriles with phosphorus pentachloride triggers a novel chloroimidate cyclization, leading directly to the corresponding annullated 4-chloropyrimidines in good to excellent yields. The reaction lends itself to the telescoped one-pot construction of 4-functionalized pyrimidines from the corresponding (hetero)aromatic 2-aminonitriles. For a pyrazolopyrimidine development intermediate, this reaction was scaled up to multikilogram scale with excellent results. A total of 10 examples with different substrates are provided. This one-pot reaction provides an attractive and sustainable alternative to the commonly used multistep methodology for this transformation.

Preparation and resolution of a modular class of axially chiral quinazoline-containing ligands and their application in asymmetric rhodium-catalyzed olefin hydroboration

The preparation and resolution of a series of axially chiral quinazoline-containing ligands is described in which the key steps are the metal-catalyzed naphthyl-phosphorus bond formation, the naphthalene-quinazoline Suzuki coupling, and the preparation of the Suzuki electrophilic components from the corresponding imidate and anthranilic acid. Diastereomeric palladacycles derived from the racemic phosphinamines and (+)-di-μ-chlorobis[(R)- dimethyl(1-(1-naphthyl)ethyl)-aminato-C2,N]dipalladium(II) were separated by fractional crystallization. The configuration of the resulting diastereomers was determined by X-ray crystallographic analysis. Displacement of the resolving agent by reaction with 1,2-bis(diphenylphosphino)ethane afforded enantiopure ligand in each case. Their rhodium complexes were prepared and applied in the enantioselective hydroboration of a range of vinylarenes. The quinazolinap catalysts were found to be extremely active, giving excellent conversions, good to complete regioselectivities, and the highest enantioselectivities obtained to date for several members of the vinylarene class, including cis-β-methylstyrene (97%), cis-stilbene (99%), and indene (99.5%).

A facile and versatile route to 2-substituted-4(3H)-quinazolinones and quinazolines

A range of 2-aryl and 2-alkyl quinazolinones have been prepared in moderate to good yields from the reaction of anthranilic acid and the appropriately substituted imidate in a facile, mild, onepot procedure. Subsequent reaction with phosphorus oxychloride afforded the corresponding 4-chloro-2-substituted quinazolines, which are useful synthetic intermediates, in good to high yields. Product isolation was facilitated by the development of work up procedures for both reactions that did not include purification by column chromatography.