Adenine → HCID 178445819, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL three-neck flask with trans-3-(triisopropyl-siloxyethyl)cyclobutyl -mesylate (0.27 g, 7.7 mmol), adenine (0.16 g, 1.18 mmol) and Cs2CO3 (0.38 g, 1.17 mmol) inside, dry DMF 5 mL was added under argon. Then began to heat to 120° C. and after 24 hr, the solvent was removed and directly applied to silica gel flash chromatography to give 0.14 g (47%) the desired product. 1H NMR (CDCl3, 400 MHz): δ 0.99-1.05 (m, 21H), 1.72-1.78 (m, 2H), 2.15-2.23 (m, 2H), 2.60-2.79 (m, 3H), 3.67-3.70 (t, J=6.0, 2H), 4.81-4.90 (m, 1H), 6.37-6.39 (bs, 2H), 7.88 (s, 1H), 8.31 (s, 1H). 13C NMR (CDCl3, 100 MHz): δ 12.08, 18.17, 26.60, 37.03, 39.84, 45.86, 61.64, 138.76, 140.09, 150.07, 152.91, 155.93. MS (FAB): expected for C20H35N5OSi (M+H)+ 390.61. Found 390.26828. IR (neat) νmax 2942, 2865, 1670, 1604, 1571, 1463, 1415, 1308, 1246, 1108, 882, 681, 658.

Provenance & Evidence