Ethylamine → HCID 11698415, compound

Participants

Reaction Steps

A mixture of 3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)aniline (25 mg, 0.063 mmol) and diisopropylethylamine (9.0 mg, 0.069 mmol) in dichloromethane (1.5 mL) was added in three portions over a period of 30 minutes to a solution of triphosgene (7.0 mg, 0.023 mmol) in dichloromethane (0.5 mL) while stirring at ambient temperature. Stirring continued for 15 minutes followed by the addition of ethylamine (0.075 mL, 2M in tetrahydrofuran). The reaction was stirred for 2 hours, then diluted with dichloromethane (30 mL) and washed with sodium bicarbonate (2×20 mL). The organic layer was dried (Na2SO4), concentrated, and purified by column chromatography over silica gel using 40% ethyl acetate in hexanes as eluant to give 15 mg (51%) of N-ethyl-N′-[3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)phenyl]urea as a white solid. MS [M+H] 467.3. 1H NMR (400 MHz, CDCl3) δ (ppm) 8.64 (s, 1H), 7.45-7.38 (m, 2H), 7.21 (s, 1H), 7.18 (t, J=8.0 Hz, 1H), 7.06-7.01 (m, 2H), 6.82 (t, J=2.4 Hz, 1H), 6.79 (m, 1H), 6.50 (m, 1H), 4.58 (t, J=6.0 Hz, 2H), 3.72 (t, J=6.0 Hz, 2H), 3.30 (q, J=7.2 Hz, 2H), 2.06 (m, 2H), 1.16 (t, J=7.2 Hz, 3H).

Provenance & Evidence