Potassium Hydroxide → 4-[3-[4-[Bis(4-fluorophenyl)methyl]-piperazin-1-yl]-2-hydroxy-propoxy]-1-(tetrahydropyran-2-yl)pyrazolo[3,4-d]pyrimidine

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A toluene solution (30 mL) of 3-[4-[bis(4-fluorophenyl) methyl]-1-piperazinyl]-1,2-propanediol (3.98 g, 11 mmol) was added dropwise to a stirred mixture of 4-chloro-1-(tetrahydropyran-2-yl)-pyrazolo[3,4-d]pyrimidine (2.387 g, 10 mmol), powdered KOH (0.485 g, 8.51 mmol), 18-crown-6 (3, 90.2 mg, 0.34 mmol) in toluene (70 mL) over a 20 min period. The mixture was stirred at room temperature for 3 h and washed with water (3×70 mL). The organic layer was dried (Na2SO4), filtered and evaporated to dryness. The oily residue (7.0 g) was purified on a medium pressure silica gel column eluting with increasing proportions of methanol in methylene chloride. The title compound was obtained as the major product (1.49 g, 41%), mp 101°-105° C. IR (KBr) cm-1 : 2466, 2446, 2401, 1603, 1568, 1506, 1347, 1222. 1H NMR (CDCl3) δ: 8.35 (s, 1H, 3 or 6-H), 8.12 (s, 1H, 3 or 6-H), 6.9-7.4 (m, 8H, Ar--H), 5.0 (m, 1H, N--O--CH--C), 4.6 (m, 2H, OCH2), 4.23 [s, 1H, CH(O)2 ], 4.15 (m, 2H, HCOH, O--CHN), 3.8 (m, 1H, OCNH), 1.6-2.9 (m, 16H, CH2, NCH2 ; MS(DCI): 565 (MH)+.

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