Dichloromethane → methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate

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Reaktionsgleichung

[CH:1]([NH:4][C@@H:5]([CH2:10][CH3:11])[C:6]([O:8][CH3:9])=[O:7])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1.ClCCl>C1CCCCC1>[Cl:17][C:18]1[N:23]=[C:22]([N:4]([CH:1]([CH3:3])[CH3:2])[C@@H:5]([CH2:10][CH3:11])[C:6]([O:8][CH3:9])=[O:7])[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

Methyl (2S)-2-(isopropylamino)butanoate 43a (10.75 g, 67.50 mmol) was dissolved in 180 mL of cyclohexane followed by the addition of sodium bicarbonate (22.68 g, 0.27 mol) and 2,4-dichloro-5-nitro-pyrimidine (15.71 g, 0.081 mol) successively, the reaction mixture was heated to 85° C. and stirred for 2.5 hours. The resulting mixture was cooled down to room temperature, added with 200 mL of dichloromethane, 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 methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate 43b (8.78 g, yield: 41.1%) as a yellow solid.

Aufarbeitung

temperatureThe resulting mixture was cooled down to room temperature
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography with elution system B

Quellen und Nachweise

ORD-Eintrag: ord-a38e9e5b319048c5a82cfea3cc1496c9
Quelldatensatz: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08691822B2

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