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0 °C

37% Aqueous formaldehyde (0.015 ml) at 0° C., was added to a stirred solution [2-[2-amino-5-[1-(4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazol-7-yl]methanol (46 mg) dissolved in dichloromethane (2 ml) and methanol (2 ml) over a period of 5 minutes. The resulting solution was stirred at 0° C. for 10 minutes. Sodium triacetoxyhydroborate (30.0 mg) was added at 0° C. to the mixture and stirred at 0° C. for 1 hour. A solution 7N of ammonia in methanol (20 ml) was added to the mixture and adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 4 to 8% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness and the product was recrystallized from acetonitrile to afford [2-[2-amino-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazol-7-yl]methanol (37.0 mg) as a solid. NMR Spectrum: (CDCl3) 2.05-2.29 (m, 6H), 2.36 (s, 3H), 2.98-3.08 (m, 2H), 4.12-4.23 (m, 1H), 5.09 (s, 2H), 6.88 (bs, 2H), 7.37 (dd, 1H), 7.43 (d, 1H), 7.66 (d, 1H), 7.67 (s, 1H), 7.74 (s, 1H), 8.30 (d, 1H), 8.32 (d, 1H); Mass spectrum: M+H+ 405;

1. stirringstirred at 0° C. for 1 hour
2. customThe crude product was purified by flash chromatography on silica gel eluting with 4 to 8% methanolic ammonia (7 N) in dichloromethane
3. customThe solvent was evaporated to dryness
4. customthe product was recrystallized from acetonitrile