Hydrochloric Acid → HCID 178466037, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of crude 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydropyrimidine-2(1H)-thione (Compound 8) (392 mg, 0.877 mmol), m-CPBA (887 mg of 85% purity, 4.38 mmol) and aqueous methylamine solution (3 mL) in ethanol (20 mL) was stirred at 0° C. for 2 h, then at room temperature overnight. Na2SO3 (2 g) was added and then dilute hydrochloride acid was added drop wise to adjust the pH to about 6. The above mixture was extracted with ethyl acetate (40 mL×3), dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography, followed by preparative HPLC twice to afford Compound 117 (26 mg, yield: 6.7%). 1H NMR (DMSO-d6 400 MHz): δ 8.73 (s, 1H), 7.83 (d, J=7.2 Hz, 1H), 7.53 (s, 1H), 7.48 (s, 2H), 7.33 (s, 4H), 7.10-7.11 (m, 3H), 7.01 (s, 1H), 6.89-6.91 (m, 3H), 5.22 (s, 1H), 3.93 (d, J=6.8 Hz, 1H), 2.78 (s, 3H), 1.24-1.27 (t, J=4.8 Hz, 3H); MS (ESI): m/z 445.2 [M+1]+.

Provenance & Evidence