HCID 11495566, compound → HCID 11646895, compound

Participants

Reaction Steps

5-(4-Fluorophenyl)-4-[3-(3-nitrophenoxy)propoxy]thieno[2,3-d]pyrimidine (250 mg, 0.588 mmol) was dissolved in tetrahydrofuran (15 mL) and added (under an atmosphere of argon) to a suspension of 25 mg of 10% palladium/carbon in methanol (30 mL) and acetic acid (5 mL). The mixture was then shaken under 40 psi of hydrogen overnight. The palladium/carbon was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate solution (2×30 mL). The organic layer was separated, concentrated, and purified by column chromatography over silica gel using 33% ethyl acetate in hexanes as eluant to give 180 mg (76%) of 3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)aniline as a colorless gum. MS [M+H] 396.1, 1H NMR (CDCl3) δ (ppm) 8.65 (s, 1H), 7.45-7.40 (m, 2H), 7.21 (s, 1H), 7.09-7.00 (m, 3H), 6.30 (d, J=2.1 Hz, 1H), 6.20 (d, J=2.8 Hz, 1H), 6.11 (s, 1H), 4.58 (t, J=6.0 Hz, 2H), 3.69 (t, J=6.0 Hz, 3H), 3.68 (b, 2H), 2.05 (m, 2H).

Provenance & Evidence