Water → 3-carboxy-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indole

HRID 1869176

Reaktionsgleichung

O.[OH-].[Li+].O.C[O:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[C:19]3[CH:26]=[CH:25][N:24]([CH3:27])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH:10]=1)=[O:8]>O1CCCC1>[C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[C:19]3[CH:26]=[CH:25][N:24]([CH3:27])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH:10]=1)([OH:8])=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

0.629 g (15 mmol) of lithium hydroxide monohydrate and 20 cm3 of water are added to 1.35 g (4.41 mmol) of 3-methoxycarbonyl-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indole dissolved in 20 cm3 of tetrahydrofuran at a temperature in the region of 20° C. After stirring for 4 hours at the reflux temperature of the solvent and for 24 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 30 cm3 of water (pH=12) and extracted with 100 cm3 of ethyl acetate. The pH is then adjusted to 6 by adding 1 N hydrochloric acid solution. The precipitate obtained is filtered off and dried at a temperature in the region of 50° C. under reduced pressure (2.7 kPa), giving 1.0 g of 3-carboxy-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indole in the form of a white powder. Mass spectrum (EI): m/e 292 (M+) (base peak).

Aufarbeitung

concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
extractionextracted with 100 cm3 of ethyl acetate
additionby adding 1 N hydrochloric acid solution
customThe precipitate obtained
filtrationis filtered off
customdried at a temperature in the region of 50° C. under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag: ord-4c28a474da9c4ad6b7298f492c723a88
Quelldatensatz: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07638521B2

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