Selective acid hydrolysis of 2-substituted-5-dimethylaminomethyleneaminopyrimidines to 5-amino- and 5-hydroxypyrimidines

Multifunctional Antioxidants for the Treatment of Age-Related Diseases

“…Compound 15 was obtained from commercially available 2-chloro-5-nitropyrimidine ( 12 ) by first reducing the nitro group to 2-chloro-5-aminoprimidine ( 13 ) by refluxing with acetic acid in the presence of iron. Subsequent diazotization of the amine 13 failed; however, 2-chloro-5-hydroxypyrimidine 15 could be obtained in poor yield (33%) by refluxing 13 with 2M sulfuric acid65.…”

“…Subsequent diazotization of the amine 13 failed; however, 2-chloro-5hydroxypyrimidine 15 could be obtained in poor yield (33%) by refluxing 13 with 2 M sulfuric acid. 65 Because of the poor yield in obtaining 15, an alternative approach to compound 2 was employed. As outlined in Scheme 3, an initial nucleophilic reaction of N,N-dimethylpiperazine-1-sulfonamide 10 with 2-chloro-5-nitropyrimidine 12 gave the nitro product 16 which was reduced to the amine 17 by refluxing with NH 4 Cl and iron.…”

Investigation of high Δεderivatives of the [closo-1-CB9H10]−anion for liquid crystal display applications

“…11) was obtained using a ligand-free Suzuki coupling reaction 12 (Scheme 5). Phenols 10h, 13 10i, 14,15 and 10l (ref. 16) were obtained as reported in the literature.…”