Potassium Carbonate → 6-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-purine

反応式

[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23]

参加物

実験手順

6-Chloropurine (5.0 g, 32 mmol) in DMF (75 mL) was treated with potassium carbonate (9.0 g, 65 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (7.0 g, 42 mmol) and stirred for 2 h. The reaction mixture was partitioned between EtOAc and water. The organic layer was dried (MgSO4), concentrated in vacuo and purified by column chromatography (SiO2, 20% EtOAc in isohexane) to give the title compound (4.9 g, 54%) as an off-white solid. δH (CDCl3) 8.82 (1H, s), 8.32 (1H, s), 5.71 (2H, s), 3.71-3.61 (2H, m), 1.03-0.93 (2H, m), 0.00 (9H, s).