反应详情

In 2 mL of ethanol, 40 mg (0.07 mmol) of (9-{4-[3-(4-formyl-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)-methyl-carbamic acid tert-butyl ester was dissolved, and 15 μL of acetic acid and 20 mg (0.20 mmol) of 1-methylpiperazine were added thereto, and the mixture solution was stirred at room temperature for 30 minutes. To the reaction solution, 10 mg (0.26 mmol) of sodium cyanoborohydride was further added and the resulting solution was stirred at room temperature for one hour. The reaction solution was concentrated and partitioned between water and ethyl acetate and the organic layer was washed with a saturated sodium chloride solution, concentrated under reduced pressure and purified by a silica gel column (ethyl acetate:methanol=4:1). The obtained intermediate was dissolved in 1 mL of trifluoroacetic acid and stirred for one hour. The reaction solution was concentrated and partitioned between a saturated sodium bicarbonate solution and ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution, concentrated under reduced pressure, and purified by trituration with ethyl acetate to obtain 27.4 mg (70%) of a target product as a white solid.

1. stirringthe resulting solution was stirred at room temperature for one hour
2. concentrationThe reaction solution was concentrated
3. custompartitioned between water and ethyl acetate
4. washthe organic layer was washed with a saturated sodium chloride solution
5. concentrationconcentrated under reduced pressure
6. custompurified by a silica gel column (ethyl acetate:methanol=4:1)
7. dissolutionThe obtained intermediate was dissolved in 1 mL of trifluoroacetic acid
8. stirringstirred for one hour
9. concentrationThe reaction solution was concentrated
10. custompartitioned between a saturated sodium bicarbonate solution and ethyl acetate
11. washthe organic layer was washed with a saturated sodium chloride solution
12. concentrationconcentrated under reduced pressure
13. custompurified by trituration with ethyl acetate