Triethylamine → 6-[1-[1-[Bis(4-fluorophenyl)methyl]piperazine-4-yl]-2-hydroxy-3-propanylthio]purine Hemihydrate

Participants

Reaction Steps

To DMF (7 mL), 6-mercaptopurine (5 mmol, 0.85 g) was added in portions and the solution was stirred at room temperature, under N2 for 5 min. Et3N (5 mmol, 0.69 mL) was added dropwise. After 5 min, 1-(1-chloro-2-hydroxy-3-propanyl)-4-[bis(4-fluorophenyl)-methyl]-piperazine (5 mmol, 1.9 g) in DMF (5 mL) was added dropwise over 5 min at room temperature under N2. After 22 h, the solution was filtered through a sintered glass funnel and the filtrate was evaporated (1.0 mm Hg, 50° C., stirring). Silica gel flash chromatography of the crude product (2.34 g) using 10% MeOH:CH2Cl2 gave pure product, 0.630 g (25.4%), mp 115°-116° C. (dec). DCI/MS (M+1) 497. 400 MHz 1H NMR (CDCl3)δ: 8.6 (s, 1H), 8.25 (s, 1H), 7.35 (m, 4H), 6.95 (m, 4H), 4.2 (s, 1H), 4.15 (m, 1H), 3.45 and 3.6 (m, 2H), 2.65 (m, 2H), 2.6 (m, 4H), 2.4 (m, 4H).

Provenance & Evidence