Reaction Steps
A sample of 2-(5-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-4H-1,2,4-triazol-3-yl)-pyridine (S64, 6 mg, 0.01 mmol) was dissolved in MeCN (142 μL) and cooled to 0° C. NaH (60%, 0.4 mg, 0.01 mmol) was added as a solid. After 5 min, MeI (1 μL) was added. Upon completion of the reaction (1.5 h), the solvent was removed in vacuo. The residue was purified by preparative thin layer chromatography (SiO2, 50% EtOAc-hexanes) to afford two separate compounds, the N1 and N2 alkylated triazoles (4.5 mg, 68%) as colorless oils. The individual N1 alkylated TBS ether (6.6 mg, 0.014 mmol) was dissolved in THF (178 μl), treated with Bu4NF (1 M in THF, 18 μL) and stirred at room temperature for 16 h under Ar. The reaction mixture was diluted with EtOAc, washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude alcohol that was purified by preparative thin layer chromatography (SiO2, 50% EtOAc-hexanes) to afford the title compound (2.0 mg, 41%) as a colorless oil (N1 isomer determined by HMBC): 1H NMR (CDCl3, 600 MHz) δ 8.68 (d, 1H, J=4.7 Hz), 8.19 (d, 1H, J=7.9 Hz). 7.82 (dt, 1H, J=1.8, 7.8 Hz), 7.35 (ddd, 1H, J=1.0, 4.8, 7.5 Hz), 7.26 (m, 2H), 7.15 (m, 3H), 4.82 (br s, 1H), 4.33 (s, 3H), 2.59 (t, 2H, J=7.7 Hz), 1.97 (m, 1H), 1.88 (m, 1H), 1.61 (m, 2H), 1.50 (m, 2H), 1.40 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 164.9, 152.3, 149.0, 148.1, 143.0, 137.1, 128.5, 128.4, 125.7, 124.2, 124.1, 68.7, 38.9, 37.1, 36.1, 31.6, 29.5, 29.4, 25.3; HRMS-ESI-TOF m/z 351.2179 ([M+H]+, C21H26N4O requires 351.2179).
