Sodium Iodide → HCID 58346558, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-(2-bromoethyl)-6-[2-(4-nitrophenyl)ethoxy]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazole (4.0 g, 7.99 mmol), K2CO3 (2.21 g, 15.99 mmol), and NaI (1.20 g, 7.99 mmol) in acetonitrile (300 mL) was added N-methyl piperazine (3.20 g, 31.98 mmol). Resulting mixture was heated at 80° C. for 4.5 h after which time analytical HPLC showed no more starting material present and a new major peak appeared. Solvents were evaporated and the residue was dissolved in water and CH2Cl2. The organic layer was separated, dried (Na2SO4), and concentrated to afford a light yellow solid. The solid material was further washed with ether, air-dried to afford a pale solid (4.14 g, 95%) as the desired product. 1H-NMR (DMSO-d6) δ 8.52 (s, 1H), 8.19 (d, 2H), 7.95 (s, 1H), 7.63 (d, 2H), 4.78 (t, 2H), 4.14 (t, 2H), 3.28 (t, 2H), 3.01 (t, 2H), 2.78 (t, 2H), 2.67 (t, 2H), 2.40 (broad, 4H), 2.26 (broad, 4H), 2.11 (s, 3H); LCMS RT=2.42 min; [M+H]+=520.2.

Provenance & Evidence