Azidotrimethylsilane → HCID 178444677, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 2-[4-(3-cyano-phenyl)-1-(2-methyl-pentyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid diethylamide (45 mg, 0.11 mmol) in 4 mL toluene at room temperature was added Bu2SnO (12 mg, 0.05 mmol) and azidotrimethylsilane (0.09 mL, 0.66 mmol). The reaction mixture was heated to 100° C. for 28 hours and cooled to room temperature. The reaction was quenched with water, neutralized with NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried and concentrated. The resulting crude material was purified by flash chromatography with 5% MeOH/CH2Cl2 to afford 25 mg (51%) of the desired tetrazole. 1HNMR (400 MHz, CDCl3) δ 8.70 (s, 2H), 8.15 (s, 1H), 7.94 (d, 1H), 7.25-7.13 (comp, 2H), 3.53-3.51 (comp, 4H), 3.25-3.22 (comp, 4H), 2.70 (br s, 6H), 1.93 (br s, 1H), 1.40-1.12 (comp, 10H), 1.01 (d, 3H), 0.81 (t, 3H); MS (M+1) 491.4.

Provenance & Evidence