41803-68-3Relevant academic research and scientific papers
Convenient and practical one-pot synthesis of 4-chloropyrimidines via a novel chloroimidate annulation
Storz, Thomas,Heid, Richard,Zeldis, Joseph,Hoagland, Steven M.,Rapisardi, Vito,Hollywood, Susan,Morton, George
, p. 918 - 924 (2012/07/14)
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.
Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, I. A Novel General Method for the Preparation of 4-Aminoquinazolines and their Hetero Analogues
Korbonits, Dezsoe,Kiss, Pal,Simon, Kalman,Kolonits, Pal
, p. 3183 - 3193 (2007/10/02)
Catalytic hydrogenation of 3-(2-aminoaryl)-1,2,4-oxadiazoles (9, 12, 15, 18, 21) to 2-amino-N-acylarenecarboxamidines (10, 13, 16, 19, 22) followed by dehydration gave condensed 4-amino-pyrimidines (11, 14, 17, 20, 23), while the corresponding secondary amines (24) afforded 1,2-disubstituted 4-iminoquinazolines (26).Reduction and dehydration of 3--1,2,4-oxadiazoles (28) provided, via a somewhat different pathway, 4-(acylamino)quinazolines (31).
