Water → 2-amino-8-phenyl-1,5,6,7,8,9-hexahydrocyclohepta[d]pyrimidin-4-one

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Reaction Steps

A mixture of Example 11A (1.86 g, 7.55 mmol), guanidine nitrate (1.84 g, 15.1 mmol), and potassium carbonate (2.09 g, 15.1 mmol) was heated in N,N-dimethylformamide (7.5 mL) at 120° C. overnight. After this time, the mixture was cooled to room temperature and poured into water. The liquid was adjusted to pH 5 with acetic acid, then the precipitate was collected by filtration, washed with water, and air-dried. It was further dried by azeotroping with toluene to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ 10.73 (m, 1H), 7.26 (m, 5H), 6.26 (s, 2H), 3.10 (s, 1H), 3.00 (dd, J=14.67, 6.35 Hz, 1H), 2.60 (t, J=13.68 Hz, 1H), 2.39 (d, J=13.48 Hz, 1H), 2.10 (m, 1H), 1.88 (m, 3H), 1.22 (m, 1H); MS (DCI+) m/z 256 (M+H)+.

Provenance & Evidence