Iodoethane → 2-Chloro-8-cyclopentyl-7,7-diethyl-5-methyl-pteridin-6-one

Temperature

-78 °C

(7S)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7H-pteridin-6-one 41f (148 mg, 0.50 mmol) was dissolved in 20 mL of tetrahydrofuran. The reaction solution was cooled down to −78° C. followed by the addition of lithium diisopropylamide (0.5 mL, 1 mmol), stirred for 30 minutes, then added with ethyl iodide (156 mg, 1 mmol) and stirred for another 4 hours. The reaction mixture was added with 50 mL of saturated ammonium chloride solution, concentrated under reduced pressure and and extracted with dichloromethane (100 mL×2). The combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively, 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 with elution system B to obtain the title compound 2-chloro-8-cyclopentyl-7,7-diethyl-5-methyl-pteridin-6-one 42a (100 mg, yield: 62.0%) as a yellow solid.

1. stirringstirred for another 4 hours
2. concentrationconcentrated under reduced pressure
3. extractionextracted with dichloromethane (100 mL×2)
4. washThe combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography with elution system B

ORD record

ord-d7c574cc08884b83abccc5c286a55efa

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691822B2