Potassium Carbonate → HCID 178504248, compound

Participants

Reaction Steps

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).

Provenance & Evidence