Tert-butyl 4-[3-(aminomethyl)phenoxy]piperidine-1-carboxylate → tert-Butyl 4-(3-{[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]methyl}phenoxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (522 mg, 1.62 mmol) and tert-butyl 4-[3-(aminomethyl)phenoxy]piperidine-1-carboxylate (544 mg, 1.78 mmol) were dissolved in MeOH (10 ml). The mixture was heated in a microwave for 30 minutes at 120° C. A precipitate was formed from MeOH. The precipitate was filtered off and washed with MeOH yielding the title compound as a white solid. Yield: 431 mg (48%). 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 7.63 (m, 2H), 7.47 (s, 1H), 7.43 (m, 2H), 7.30-7.25 (m, 1H), 6.95-6.91 (m, 2H), 6.86 (m, 1H), 5.19 (s, 2H), 4.46 (m, 1H), 3.67 (m, 2H), 3.33 (m, 2H), 1.94-1.85 (m, 2H), 1.77-1.67 (m, 2H), 1.54 (s, 9H).

Provenance & Evidence