Dimethyl Sulfate → HCID 178495813, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 140C (120 mg, 0.34 mmol) in tetrahydrofuran (5 mL) were added potassium tert-butoxide (83 mg, 0.75 mmol) and dimethyl sulfate (95 mg. 0.75 mmol). The reaction mixture was stirred at 75° C. for 16 hours, then cooled, quenched with saturated aqueous NaHCO3 (5 mL) and extracted with ethyl acetate (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash 280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.54-1.70 (m, 4H), 1.73-1.92 (m, 4H), 2.13-2.24 (m, 2H), 2.30 (s, 1H), 2.67 (t, J=6.8 Hz, 2H), 3.33 (s, 3H), 3.36 (s, 3H), 3.64-3.73 (m, 2H), 4.22-4.30 (m, 2H), 4.42 (s, 2H), 6.95 (s, 1H); MS (ESI+) m/z 351 (M+H)+; Anal. Calculated for C18H26N2O3S: C, 61.69; H, 7.48; N, 7.99. Found: C, 61.93; H, 7.62; N, 7.68.

Provenance & Evidence