Sodium Hydroxide → 6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo(3,4-b)pyrazin-5-one

HRID 1876774

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[C:9]2=[O:18])=[N:6][CH:7]=1.[BH4-].[Na+].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:9]([OH:18])[C:10]3[C:15](=[N:14][CH:13]=[CH:12][N:11]=3)[C:16]2=[O:17])=[N:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 2.5 °C

Versuchsvorschrift

6-(5-Chloropyridin-2-yl)-5,7-dioxo-5,6-dihydropyrrolo-[3,4-b]-pyrazine (100g) was suspended in 900 ml water. The slurry was cooled to 0-5° C. and 100 ml (7.2%) of aqueous sodium borohydride solution stabilized with 0.1 g sodium hydroxide was added in 3 hrs under vigorous stirring. Reaction mixture was stirred at 0-5° C. for 4 to 5 hrs. After completion of reaction solid was filtered and washed with 2×300 ml water. The filtered solid was refluxed in 215 ml dichloromethane for 30 min and cooled to 25-30° C. The solid was filtered, washed with 100 ml dichloromethane and dried at 50-60° C. to obtain 82 g of title compound.

Aufarbeitung

additionwas added in 3 hrs under vigorous stirring
customReaction mixture
customAfter completion of reaction solid
filtrationwas filtered
washwashed with 2×300 ml water
temperatureThe filtered solid was refluxed in 215 ml dichloromethane for 30 min
temperaturecooled to 25-30° C
filtrationThe solid was filtered
washwashed with 100 ml dichloromethane
customdried at 50-60° C.

Quellen und Nachweise

ORD-Eintrag: ord-79b62fd05b514b80a74caa439c8ca8ca
Quelldatensatz: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08309723B2

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