Tetrahydrofuran → HCID 49873136, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-amino-2-ethylquinazolin-4(3H)-one (Aldrich, 150 mg, 0.79 mmol) and Example 54B (144 mg, 0.79 mmol) in tetrahydrofuran (10 mL), a solution of 1-propanephosphonic acid cyclic anhydride (Aldrich, 50% w/w in ethyl acetate (0.6 mL, 0.95 mmol) was added followed by triethylamine (0.22 mL, 1.60 mmol). The reaction mixture was stirred at 80° C. overnight and quenched with 1M NaHCO3 (10 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% of EtOAc in hexanes) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.21 (t, J=7.3 Hz, 3 H), 1.64-1.81 (m, 2 H), 1.81-2.07 (m, 8 H), 2.14-2.29 (m, 2 H), 2.51-2.79 (m, 2H), 4.22-4.32 (m, 1 H), 7.49-7.57 (m, 1 H), 7.66 (d, J=7.5 Hz, 1 H), 7.80-7.89 (m, 1 H), 8.09 (dd, J=8.0, 1.2 Hz, 1 H), 10.59 (s, 1 H); MS (ESI+) m/z 354 (M+H)+; Elemental Analysis: Calculated for C20 H23N3O3: C-67.97; H-6.56, N-11.89. Found: C-67.7; H-6.8; N-11.89.

Provenance & Evidence