Hydrochloric Acid → HCID 67061123, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,2-diphenylethanone (53 mg, 0.270 mmol), ethyl 2-ethoxy-4-formylbenzoate (Intermediate 48) (50 mg, 0.225 mmol) and urea (41 mg, 0.675 mmol) in EtOH (2.5 mL) was added concentrated HCl (0.1 mL). The mixture was stirred at 90° C. for 16 h. The volatiles were removed under reduced pressure to afford crude ethyl 2-ethoxy-4-(2-oxo-5,6-diphenyl-1,2,3,4-tetrahydropyrimidin-4-yl)benzoate, which was dissolved in THF/H2O/MeOH (v/v/v=1/1/1, 0.6 mL) followed by addition of lithium hydroxide monohydrate (14 mg, 0.338 mmol). The solution was stirred at room temperature overnight. Most of THF and MeOH were evaporated under reduced pressure and the resulting aqueous solution was acidified with 10% hydrochloric acid to pH=6.0. The resulting precipitate was purified by prep-HPLC to afford Compound 97 as a white powder (11 mg, 12%). 1H NMR (MeOH-d4 500 MHz): δ 7.68 (d, J=8.0 Hz, 1H), 7.14 (s, 5H), 6.94-6.98 (m, 4H), 6.89 (s, 1H), 6.76 (t, J=3.5 Hz, 2H), 5.26 (s, 1H), 3.90-4.00 (m, 2H), 1.27 (t, J=7.0 Hz, 3H); MS (ESI): m/z 415.1 [M+1]+.

Provenance & Evidence