反应详情

温度

80 °C

NaH (60 mg, 1.5 mmol. 60% in mineral oil) is added to a solution of butane-2-thiol (170 μL, 1.5 mmol) in THF (5 mL). After 10 minutes, 2-chloro-5-(2,4-dimethoxy-phenyl)-3,6-diethyl-pyrazine (100 mg, 0.33 mmol) in THF (1 mL) is added dropwise, and the mixture heated at 80° C. (oil bath temperature) for 16 hours. After extractive work-up, preparative thin layer chromatography (hexanes) furnishes the title compound as a clear oil (60 mg, 51%). NMR (CDCl3, 400 MHz) H-1: 7.19 (1H, d, J=8.4 Hz), 6.58 (1H, dd, J=2.4, 8.4 Hz), 6.60 (s, 1H, J=2.4 Hz), 3.99 (sext, 1H, J=6.8 Hz), 3.85 (3H, s), 3.75 (3H, s), 2.81 (2H, q, J=7.4 Hz), 2.58 (2H, br q, J=6.8 Hz), 1.6–1.9 (m, 4H), 1.44 (3H, d, J=6.4 Hz), 1.28 (t, 3H, J=7.6 Hz), 1.19 (3H, t, J=7.6 Hz), 1.06 (t, 3H, J=7.2 Hz). C-13: 161.10, 157.86, 153.49, 151.79, 151.67, 144.47, 131.68, 121.18, 104.78, 98, 60, 55.44, 55.33, 40.87, 29.65, 27.54, 27.08, 20.56, 12.43, 12.09, 11.51. MS: 414.2 (+1, positive mode) and 412.2 (M−1, negative mode).