Iodine → HCID 11719282, compound

Participants

Reaction Steps

6-Trifluoromethyl-9-methyl-2-phenethylaminopurine (compound 10) (0.500 g, 1.56 mmol) was dried in vacuo at 100° C. for 2.5 h. After cooling, dry THF (18 ml) was added at room temperature and the solution was cooled to −72° C. (ethanol/dry ice). After addition of n-BuLi (2.4 ml of a 1.6 M solution in hexane, 3.9 mmol) the colourless solution turned yellow. After 15 minutes I2 (0.633 g, 2.49 mmol) was added and after 5 minutes the reaction was complete (HPLC: Rt,product=4.7). To the red solution silica gel (˜4 g) was added and the suspension was evaporated to dryness. Flash chromatography (1% MeOH in MTBE) and freezedrying afforded the product (0.637 g, 91%) as fluffy white crystals, mp 139-142° C. 1H-NMR (400 MHz, CDCl3), δ [ppm]: 7.33-7.21 (m, 5H, Har), 5.96 (br s, 1H, NH), 3.93 (br m, 2H, NHCH2), 3.77 (s, 3H, CH3), 2.98 (t, J=7.1 Hz, 2H, CH2). 19F-NMR (500 MHz, CDCl3), δ [ppm]: −70.12 (6-CF3).

Provenance & Evidence