Reaction Steps
A solution of 3-{[6-chloro-5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutane-1-carbaldehyde (223 mg, 0.50 mmol), 7-[(3aS,4R,6R,6aR)-2,2-dimethyl-6-[(propan-2-ylamino)methyl]-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (172 mg, 0.50 mmol) and MgSO4 (600 mg, 5.00 mmol) in DCE (10 ml) was stirred for 15 min. STAB (148 mg, 0.70 mmol) was then added to the reaction mixture and stirred for 1 h at RT. The reaction was monitored by LCMS, no amine was seen after 2.5 h. Sat. NaHCO3 (20 ml) was added to the reaction mixture and stirred for 5 mins. Brine (20 ml) was then added to the reaction mixture. The product was extracted with DCM (2×30 ml), dried over Na2SO4, filtered and evaporated. Purification by prep. HPLC gave the desired product (174 mg, 45%) as a white solid; MS (ESI+) for C38H53ClF3N7O3Si m/z 776.30 [M+H]+; HPLC purity 100% (ret. time, 1.68 min); 1H NMR (500 MHz, MeOD) δH ppm −0.25-0.11 (9H, m), 0.90 (2H, td, J=7.88, 3.47 Hz), 1.30 (3H, s), 1.37 (6H, t, J=7.49 Hz), 1.55 (3H, s), 1.63-1.84 (1H, m), 1.99-2.37 (2H, m), 2.37-3.03 (6H, m), 3.04-3.28 (3H, m), 3.34-3.50 (1H, m), 3.61 (2H, td, J=7.92, 2.29 Hz), 3.79 (1H, br. s.), 4.68 (1H, t, J=6.70 Hz), 4.95-5.27 (2H, m), 5.55-5.81 (1H, m), 6.88 (1H, d, J=3.63 Hz), 7.06-7.62 (2H, m), 7.61-7.94 (1H, m), 7.94-8.16 (1H, m), 8.22 (1H, s)
