Reaction Steps
7-[(3aS,4R,6R,6aR)-6-({[4-(5-tert-Butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)butyl]amino}methyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-N-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.052 g, 0.074 mmol) was dissolved in dry DCM (1 ml) and dry Et3N (0.02 ml, 0.148 mmol) and methanesulfonyl chloride (0.01 ml, 0.089 mmol) was added dropwise at r.t. under N2. The reaction was left for 3 hrs after which time LCMS analysis showed the reaction had gone to −80% completion. The reaction was concentrated in vacuo and purified by UV directed prep HPLC to give the product as a white solid (0.028 g, 48%): MS (ESI+) for C40H61N7O5SSi m/z 391.3 [M+2H]2+, 780.1 [M+H]+; LC purity 83% (UV), 100% ELS (ret. time, 1.80 min); 1H NMR (500 MHz, CDCl3) δ 8.29 (s, 1H), 7.59-7.79 (m, 1H), 7.29-7.45 (m, 2H), 6.97 (d, J=3.63 Hz, 1H), 6.64 (br. s., 1H), 5.50 (s, 2H), 4.88-5.06 (m, 2H), 4.58 (br. s., 1H), 3.51-3.60 (m, 2H), 3.39-3.51 (m, 1H), 3.32 (br. s., 3H), 2.98 (br. s., 3H), 2.84-2.92 (m, 3H), 2.46 (br. s., 2H), 2.16 (d, J=11.66 Hz, 1H), 1.90-2.02 (m, 2H), 1.77-1.89 (m, 2H), 1.48-1.58 (m, 3H), 1.33-1.44 (m, 9H), 1.20-1.32 (m, 4H), 0.83-0.99 (m, 4H), 0.61-0.78 (m, 2H), −0.12-0.03 (m, 9H).
