Imidazole → HCID 59380441, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-(2-bromoethyl)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}[1]benzothieno[2,3-d]pyrimidin-4-amine (40 mg, 0.07 mmol, 1 equiv) in DMF were added sodium iodide (11 mg, 0.07 mmol, 1 equiv), sodium carbonate (16 mg, 0.15 mmol, 2 equiv), and imidazole (10 mg, 0.15 mmol, 2 equiv). The resulting mixture was heated at 80° C. for 14 h. The reaction was cooled to rt and then concentrated in vacuo. The resulting crude material was purified by prep-TLC (10% methanol/DCM) and afforded a yellow solid (17.9 mg, 0.03 mmol, 45%). 1H-NMR (CD3OD) δ 8.40 (s, 1H), 8.24 (d, J=8.3 Hz, 1H), 7.71 (m, 2H), 7.45-7.36 (m, 3H), 7.28 (d, J=8.1 Hz, 2H), 7.23 (d, J=9.6 Hz, 1H), 7.10 (d, J=8.1 Hz, 1H), 7.09 (s, 1H), 7.04 (td, 1H), 6.92 (s, 1H), 5.12 (s, 2H), 4.35 (t, 2H), 3.23 (t, 2H); LCMS RT=3.22 min, [M+H]+=530

Provenance & Evidence