(R)-methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoate → (R)-2-chloro-7-ethyl-8-isopropyl-7,8-dihydropteridin-6(5H)-one

HRID 2364717

Reaktionsgleichung

[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH:16]([CH3:18])[CH3:17])[C@H:9]([CH2:14][CH3:15])[C:10](OC)=[O:11])[C:5]([N+:19]([O-])=O)=[CH:4][N:3]=1.[H][H]>C(O)(=O)C.[Ni]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:19][C:10](=[O:11])[C@@H:9]([CH2:14][CH3:15])[N:8]([CH:16]([CH3:18])[CH3:17])[C:6]=2[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

Methyl (2R)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate 22b (7.30 g, 23 mmol) was dissolved in 100 mL acetic acid followed by the addition of 5 g Raney nickel, repeated filled with hydrogen for three times. The reaction mixture was heated to 75° C., stirred for 2 hours and filtered. The filtrate was concentrated under reduced pressure, added with 30 mL of ice water resulting in the formation of precipitate. The precipitate was filtered. the filter cake was dried by heat to obtain the crude title compound (7R)-2-chloro-7-ethyl-8-isopropyl-5,7-dihydropteridin-6-one 22c (12.10 g, yield: 71.7%) as a gray solid, which was used in the next step without further furification.

Aufarbeitung

filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
additionadded with 30 mL of ice water resulting in the formation of precipitate
filtrationThe precipitate was filtered
customthe filter cake was dried
temperatureby heat

Quellen und Nachweise

ORD-Eintrag: ord-2eed172f56464660914b9bf4d77a4b28
Quelldatensatz: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08691822B2

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