Tributylstannane → N-isopropyl-6-(tributylstannyl)pyrazin-2-amine

반응식

[CH2:1]([SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Li+].CC([N-]C(C)C)C.Cl[C:23]1[N:28]=[C:27]([NH:29][CH:30]([CH3:32])[CH3:31])[CH:26]=[N:25][CH:24]=1>C1COCC1>[CH:30]([NH:29][C:27]1[CH:26]=[N:25][CH:24]=[C:23]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13])[N:28]=1)([CH3:32])[CH3:31]

참가 물질

실험 절차

To a solution of tributyl tin hydride (8.5 mL, 29.23 mmol, Aldrich) in THF (50 mL) was added LDA (2.0 M) (THF/heptane/ethyl benzene) (18.3 mL, 29.23 mmol, Aldrich) at 0° C. and the mixture was stirred for 10 min at RT. To the mixture at 0-5° C. was added 6-chloro-N-isopropylpyrazin-2-amine (2.5 g, 14.61 mmol) and the mixture was stirred for an additional 3 h at RT. The reaction was quenched with 10% aq KF (25 mL) and extracted with EtOAc (2×25 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was further purified with basic alumina column chromatography (eluent: 10% EtOAc in petroleum ether) to give N-isopropyl-6-(tributylstannyl)pyrazin-2-amine (2 g, 26.5%) as a colorless liquid. MS (ESI, pos. ion) m/z: 428.2 (M+1); 1H-NMR (400 MHz, CDCl3): δ 7.77 (s, 1H), 7.64 (s, 1H), 4.28-4.23 (m, 1H), 4.09-3.98 (m, 1H), 1.63-1.54 (m, 7H), 1.39-1.23 (m, 14H), 1.12-1.08 (m, 6H), 0.91-0.88 (q, 6H).