✍ Scribed by Yasser M. Loksha
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magnified image Treatment of 2,4,6‐trichloropyrimidines (1a, 1b) with the sodium salt of benzyl cyanide derivatives (2a, 2b) afforded 5‐substituted 4‐aryl(cyanomethyl)‐2,6‐dichloropyrimidines (3a, 3b, 3c, 3d, 3e, 3f). Compounds 3a, 3b were alkylated with methyl iodide to furnish 4‐(1‐aryl‐1‐cyanoethyl)‐2,6‐dichloropyrimidines (4a, 4b). Compounds 3a, 3b, 3c, 3d, 3e, 3f and 4a, 4b were hydrolyzed with concentrated hydrochloric acid to afford 5‐substituted 6‐arylalkyluracils 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h. 5‐Bromo‐6‐arymethylluracils (6a, 6b, 6c, 6d) were synthesized by bromination of 6‐arylmethylluracils (5a, 5b, 5c, 5d) with N‐bromosuccinimide (NBS). Refluxing 2‐(2,6‐dichloro‐5‐ethylpyrimidin‐4‐yl)‐2‐(3,5‐dimethylphenyl)acetonitrile (3f) with sodium methoxide followed by oxidation afforded (3,5‐dimethylphenyl)(5‐ethyl‐2,6‐dimethoxypyrimidin‐4‐yl)methanone (7). Addition of methylmagnesium bromide to compound 7 gave the tertiary alcohol derivative 8 which was fluorinated by diethylaminosulfurtrifluoride and deprotected by trimethylsilyl iodide to furnish 6‐(1‐(3,5‐dimethylphenyl)‐1‐fluoroethyl)‐5‐ethylpyrimidine‐2,4(1__H__,3__H__)‐dione (12). J. Heterocyclic Chem., (2009).
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A new synthetic route was developed for the synthesis of 4,6-diaryl-2-methyl-1,3-benzoxazoles and their hydrogenated derivatives. The target compounds were obtained via the Neber rearrangement from 3,5diaryl-2-cyclohexen-1-ones. The formation of the isomers in the dihydro derivatives was explained b
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