Water → 2-Chloro-6-benzylamino-9-(2-propynyl)purine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-6-benzylaminopurine (1.1 g, 3.8 mmol), in DMSO (5 mL) was cooled to 0° C., potassium carbonate (0.79 g, 5.7 mmol) and propargyl bromide (0.45 g, 3.8 mmol) was added to the contents, and stirred for 1 h at 0° C. Water (20 mL) was then added to the reaction mixture, and the resulting yellow precipitate was filtered and washed with excess water (50 mL). Compound 5 (1.1 g, 80%) was obtained as an off-white solid upon successive recrystallization from dichloromethane and ethyl acetate: mp 180° C.; EI/MS (m/z (relative %)): 297 (63, M+.), 298 (15), 299 (23), 258 (46), 91(100); 1H NMR (400 MHz, DMSO) δ 8.23 (s, 1H), 7.21-7.38 (m, 5H), 5.03 (bs, 2H), 4.62 (d, J=6 Hz, 2H), 3.51 (s, 1H). 13C NMR (100 MHz, DMSO) δ 155.6 (s), 154.0 (s), 150.3 (s), 140.7 (d, 1JC—H=214 Hz) 139.9 (s), 128.9 (d, 1JC—H=159 Hz), 127.9 (d, 1JC—H=157 Hz), 126.8 (d, 1JC—H=158 Hz), 118.1 (s), 78.5 (t, 2JC—H=9 Hz) 76.7 (dt, 1JC—H=252 Hz, 3JC—H=4 Hz), 43.8 (t, 1JC—H=126 Hz), 33.3 (t, 1JC—H=139 Hz).

Provenance & Evidence