Hydrochloric Acid → 4-Methyl-2-[2-(methylthio)-4-pyrimidinyl]benzenamine

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Reaction Steps

24 g 2,2-dimethyl-N-[4-methyl-2-[2-(methylthio)-4-pyrimidinyl]phenyl]propanamide was dissolved in 120 mL glacial acetic acid and the mixture warmed to reflux when 60 mL 15% hydrochloric acid solution was gradually added. After the addition was completed, the reaction mixture was heated at reflux for 4 h. After cooling, volatiles were removed in vacuo, the residue was taken up in 200 mL water and ice was added. The resulting mixture was neutralized to pH 10 with 5% sodium hydroxide solution and extracted with ether. Organic extracts were washed with brine, dried, evaporated to dryness and then dried in a vacuum oven to yield 6.2 g of the title compound as a tan solid melting at 120°-123° C. 1H NMR (CDCl3): δ 2.30 (s,3H), 2.60 (s,3H), 5.8 (s,2H,NH2), 6.60-8.6 (5H).

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