Benzyl Bromide → 2-Chloro-6-benzylamino-9-(1-benzyl-1H-1,2,3-triazol-4-yl-methyl)purine

Participants

Reaction Steps

Benzyl bromide (110 mg, 0.58 mmol) was added dropwise to a solution of sodium azide (42 mg, 0.64 mmol) in DMSO (5 mL, and stirred at room temperature for 15 min. Compound 5 (173 mg, 0.58 mmol), triethylamine (6 mg, 0.06 mmol) and CuBr (8 mg, 0.6 mmol) were added to the contents in that order, and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was poured into ice-cold water (20 mL), and the resulting off-white precipitate was filtered and washed with dilute NH4OH (20 mL) and water (50 mL) to give the compound 6 (200 mg 80%) essentially pure by NMR; mp 235° C. EI/MS (m/z (relative %)): 430 (32, M+.), 431 (11), 432 (13), 258 (54), (100); 1H NMR (400 MHz, DMSO) δ 8.23 (s, 1H), 8.15 (s, 1H), 7.40-7.17 (m, 10H), 5.56 (s, 2H), 5.40 (s, 2H), 4.62 (d, J=6 Hz, 2H); 13C NMR (100 MHz, DMSO) δ 155.6 (s), 153.9 (s), 150.3 (s), 143.1 (d, 1JC—H=199 Hz), 141.9 (s), 139.9 (s), 136.51 (s), 129.4 (d, 1JC—H=160 Hz), 128.9 (d, 1JC—H=159 Hz), 128.8 (d, 1JC—H=159 Hz), 128.5 (d, 1JC—H=158 Hz), 127.9 (overlapping doublets), 127.4 (overlapping doublets), 124.4 (d, 1JC—H=200 Hz) 118.6 (s), 53.4 (t, 1JC—H=145 Hz), 43.7 ((t, 1JC—H=135 Hz), 38.9 (t, 1JC—H=139 Hz).

Provenance & Evidence