反应详情

A solution of 0.31 g (2.0 mmol) of 6-chloro-1H-purine and 0.83 g (6.0 mmol) of potassium carbonate in 15 mL of DMF was stirred at 25° C. for 20 min. under argon. To it, 0.53 mL (3.0 mmol) of 1-(chloromethoxy)-2-(trimethylsilyl)ethane (SEM-Cl) was added via syringe, the solution was stirred for 9 h, filtered through Celite, and the filtrate was diluted with diethyl ether, washed with water, and brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a gradient mixture of hexane and ethyl acetate to give 0.35 g (61% yield) of 115 and 0.08 g (14% yield) of 6-chloro-3-[(2-trimethylsilylethoxy) methyl]-1H-purine (117). Compound 115: mp 33-34° C.; NMR δ 8.70 (s, 1H), 8.24 (s, 1H), 5.62 (s, 2H, NCH2O), 3.60 (t, J=8 Hz, 2H, CH2O), 0.94 (t, J=8 Hz, 2H, CH2Si), −0.12 (s, 9H, MeSi); 13C NMR δ 152.4, 152.2, 151.3, 145.4, 131.5, 72.7 (CN), 67.8 (CO), 17.8, 21.4 (CSi).

1. filtrationfiltered through Celite
2. additionthe filtrate was diluted with diethyl ether
3. washwashed with water, and brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customcolumn chromatographed on silica gel using
7. additiona gradient mixture of hexane and ethyl acetate