(R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)butanoate → HCID 24739252, compound

Temperature

77.5 °C

Methyl (2R)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate 1m (1 g, 3 mmol) was dissolved in 10 mL of acetic acid followed by the addition of Raney nickel (0.50 g), filled with hydrogen three times, then heated to 75-80° C. and stirred for 12 hours. The reaction mixture was filtered, washed with dichloromethane (50 mL). The filtrate was concentrated under reduced pressure, added with 100 mL ethyl acetate, washed with water (50 mL×3) and saturated sodium chloride solution (50 mL×3) successively. The combined organic phase was 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 (7R)-2-chloro-8-cyclopentyl-7-ethyl-7,8-dihydro-5H-pteridin-6-one 1n (0.56 g, yield: 66.7%) as a white solid.

1. filtrationThe reaction mixture was filtered
2. washwashed with dichloromethane (50 mL)
3. concentrationThe filtrate was concentrated under reduced pressure
4. additionadded with 100 mL ethyl acetate
5. washwashed with water (50 mL×3) and saturated sodium chloride solution (50 mL×3) successively
6. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-2e40d20f27b748ce9de5fe5a6847c872

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691822B2