To a solution of N-(2-bromo-4-methyl-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2H-tetrazol-5-amine (76 mg, 0.135 mmol) in anhydrous THF (5 mL) was added sodium carbonate (28 mg, 0.270 mmol) and N,N-dimethylformamide (1 mL) followed by dimethyl sulfate (34 mg. 0.270 mmol). The solution was heated to 70° C. for 18 hours then the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (20 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL) and the combined organics were washed with water (3×20 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (76 mg, 97.5%). 1H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H) 7.62 (s, 2H) 7.44(s, 1H) 7.40(s, 1H) 4.79(s, 2H) 4.76(s, 2H) 4.20(s, 3H) 2.39(s, 3H). LC-MS calc. 576 found 577 (M+H)
