Chlorotrimethylsilane → HCID 118983440, compound

Participants

Reaction Conditions

Reaction Steps

2′-C-Methylcytidine (38.9 mmol) was dissolved in pyridine (270 mL) and the reaction mixture was cooled down to 0° C. TMSCl (233.4 mmol) was added and the mixture was stirred at room temperature during 4 hours. DMAP (38.9 mmol) and mMTrCl (77.25 mmol) were added and the reaction mixture was stirred at 50° C. during 2 days. The reaction was cooled down to room temperature and a saturated solution of NaHCO3 was added slowly. The mixture was extracted with CH2Cl2 and the organic layer was dried over Na2SO4, filtered and concentrated. Co-evaporations with toluene and CH2Cl2 were done. The crude was dissolved in CH3OH (500 mL) and NH4F (194.5 mmol) was added. The reaction mixture was heated at reflux and stirred during 1 hour. The reaction mixture was cooled down to room temperature and concentrated. The crude was purified by chromatography on a silica gel column (eluent: CH2Cl2/CH3OH 0 to 10%) to give the expected compound as a yellow powder in 89% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.08 (s, 3H), 3.71-3.84 (m, 2H), 3.81 (s, 3H), 3.90-3.94 (m, 1H), 3.99-4.03 (m, 1H), 5.14 (d, J=7.63 Hz, 1H), 5.31 (s, 1H), 5.79 (brs, 1H), 6.84 (d, J=8.65 Hz, 2H), 7.13 (d, J=8.69 Hz, 2H), 7.21 (d, J=7.35 Hz, 4H), 7.27-7.34 (m, 8H), 7.51 (brs, 1H).

Provenance & Evidence