Methyl 2-((dimethylamino)methyleneamino)-5,5-dimethylcyclohex-1-enecarboxylate → 6,6-Dimethyl-3,4,5,6,7,8-hexahydroquinazolin-4-one

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A solution of methyl 2-((dimethylamino)methyleneamino)-5,5-dimethylcyclohex-1-enecarboxylate (9.5 g, 40 mol) in 7.0M ammonia in methanol (35 mL) was stirred at 25° C. for 90 minutes then concentrated to an oil. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8) to give 6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4(3H)-one (6.41 g, 90% yield) as a white solid. 1H NMR (400 MHz, d6-DMSO): 7.96 (s, 1H), 2.52 (t, 2H), 2.14 (s, 2H), 1.48 (t, 2H), 0.93 (s, 6H); MS (EI) for C10H14N2O: 179 (MH+).

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