Lithium borohydride → HCID 178418978, Verbindung

HRID 7617

Reaktionsgleichung

C[O:2][C:3]([C:5]1[N:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[CH:14][CH:13]=2)[N:8]=[C:7]([NH:23][C:24]2[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=2)[CH:6]=1)=O.[BH4-].[Li+]>C1COCC1>[OH:2][CH2:3][C:5]1[N:10]=[C:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[CH:16][CH:17]=2)[N:8]=[C:7]([NH:23][C:24]2[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=2)[CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of [6-methoxycarbonyl-2-(4-propionylamino-phenyl-sulfanyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (2 g, 4.85 mmol) in THF (100 mL) is added lithium borohydride (0.32 g, 14.5 mmol). The reaction mixture is stirred at 50° C. for 1.5 hours. The reaction is then quenched with dilute HCl and extracted with ethyl acetate. The organic layer is successively washed with aqueous saturated NaHCO3 and brine, dried over MgSO4 and evaporated. The solid residue is triturated in ethyl acetate and the resulting white solid is collected by filtration to give the desired product [6-hydroxymethyl-2-(4-propionylamino-phenyl-sulfanyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.

Aufarbeitung

customThe reaction is then quenched with dilute HCl
extractionextracted with ethyl acetate
washThe organic layer is successively washed with aqueous saturated NaHCO3 and brine
dry with materialdried over MgSO4
customevaporated
customThe solid residue is triturated in ethyl acetate
filtrationthe resulting white solid is collected by filtration

Quellen und Nachweise

ORD-Eintrag: ord-7ca708bf4bfc4bdf89b496425cc3395e
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07087603B2

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