methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate → (7S)-2-chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one

Temperatur

65 °C

Methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate 41d (14.17 g, 41.33 mmol) was dissolved in 300 mL of acetic acid followed by the addition of iron powder (9 g, 0.17 mol). After exothermic reaction was completed, the reaction solution was heated to 65° C., and stirred for 1.5 hours. The reaction mixture was filtered and the filter cake was washed with dichloromethane (350 mL). The filtrate was concentrated under reduced pressure, added with 150 mL of water and filtered. The filter cake was washed with water (60 mL×3) and the mixture solvent of hexane and acetone (V/V=6:1) (140 mL) successively. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the title compound (7S)-2-chloro-8-cyclopentyl-7-ethyl-5,7-dihydropteridin-6-one 41e (10.67 g, yield: 92.0%) as a light yellow solid.

1. customAfter exothermic reaction
2. filtrationThe reaction mixture was filtered
3. washthe filter cake was washed with dichloromethane (350 mL)
4. concentrationThe filtrate was concentrated under reduced pressure
5. additionadded with 150 mL of water
6. filtrationfiltered
7. washThe filter cake was washed with water (60 mL×3)
8. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-2b73a324c9104174a89a9f9fb2166c92

Quelldatensatz

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08691822B2