N,N,N',N'-Tetramethylazodicarboxamide → HCID 59380424, compound

Participants

Reaction Steps

To a solution of 4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-ol (50 mg, 0.11 mmol, from Example 34) in THF (2 mL) was added triphenylphosphine (43.5 mg, 0.17 mmol, 1.5 equiv) and 1,1′-Azobis(N,N-dimethylformamide) (28.6 mg, 0.17 mmol, 1.5 equiv) under nitrogen. The reaction mixture was stirred at rt for 5 mins and 4-(2-hydroxyethyl)morpholine (21.8 mg, 0.17 mmol, 1.5 equiv) was then. The reaction mixture was stirred at rt for 15 h and it was concentrated in vacuo. The crude material was purified by preparative HPLC to give N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-7-(2-morpholin-4-ylethoxy)[1]benzothieno[2,3-d]pyrimidin-4-amine as a white solid (18.1 mg, 29%). 1H-NMR (DMSO-d6) δ 8.08 (broad s, NH), 7.65 (s, 1H), 7.62 (d, J=9.2 Hz, 1H), 6.91 (m, 2H), 6.74 (m, 3H), 6.63 (m, 1H), 6.48-6.37 (m, 3H), 4.42 (s, 2H), 3.38 (t, 2H), 2.75 (t, 4H), 1.90 (t, 2H), 1.65 (t, 4H), LCMS RT=2.75 min, [M+H]+=565.20.

Provenance & Evidence