Iodoethane → HCID 10387392, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 8-bromo-7-(2-chloro-6-fluorobenzyl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione (200 mg, 0.52 mmol) and K2CO3 (357 mg, 2.6 mmol) in 4 mL DMF was treated with iodoethane (412 μL, 5.2 mmol). The reaction was heated to 50° C. for 48 hr. The reaction mixture was cooled, diluted with H2O, and extracted 3× with 50% EtOAc:hexanes. The organic layers were combined and the solvent removed under reduced pressure (116 mg, 54% yield). The crude product (52 mg, 0.13 mmol) was dissolved in 200 μL DMSO and treated with piperidine (37 μL, 0.38 mmol). The reaction mixture was heated to 100° C. for 15 hr. The reaction mixture was cooled, diluted with H2O, and extracted 3× with 50% EtOAc:hexanes. The organic layers were combined, dried with Mg2SO4, and evaporated under reduced pressure. The crude product was purified by preparative thin layer chromatography (silica gel, 1 mm plate, EM Science 20×20 cm silica gel 60 F264) eluting with EtOAc:hexane (1:1) to give 31 mg (56% yield) of the title compound as a white solid: 1H NMR (CDCl3, 400 MHz) 7.21-7.14 (m, 1H), 7.13-7.09 (m, 1H), 6.96-6.90 (m, 1H), 5.53 (s, 2H), 3.96 (q, 2H, J=7.0 Hz), 3.49 (s, 3H), 3.09-3.00 (m, 4H), 1.54-1.46 (m, 6H), 1.13 (t, 3H, J=7.0 Hz); MS (ESP+) m/e 420 (MH+).

Provenance & Evidence