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The crude compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(morpholin-2-ylmethyl)-2,3-dihydrobenzofuran-4-carboxamide 2f (163 mg, 0.30 mmol) was dissolved in 60 mL of the mixture solvent of acetonitrile and water (V/V=1:1) in an ice-water bath, the reaction solution was cooled down to 0° C. followed by the addition of formaldehyde (18 mg, 0.60 mmol) and sodium triacetoxyborohydride (191 mg, 0.90 mmol), warmed up slowly to room temperature and stirred for 2 hours. The resulting mixture was added dropwise with saturated sodium bicarbonate solution to adjust pH to 9 to 10, extracted with dichloromethane (50 mL×3). The combined organic phase was washed with saturated sodium chloride solution (50 mL×3), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-[(4-methylmorpholin-2-yl)methyl]-2,3-dihydrobenzofuran-4-carboxamide 2 (62 mg, yield: 38.0%) as a white solid.

1. temperaturewarmed up slowly to room temperature
2. extractionextracted with dichloromethane (50 mL×3)
3. washThe combined organic phase was washed with saturated sodium chloride solution (50 mL×3)
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography