1-Butanol → 4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid

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Reaktionsgleichung

[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH:12]([F:14])[F:13])=[CH:8][C:7]=2[C:15]2[C:16]3[NH:23][C:22]([CH3:24])=[C:21]([C:25]([O:27]CC)=[O:26])[C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:3][CH2:2]1.C(O)CCC.CC([O-])(C)C.[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH:12]([F:14])[F:13])=[CH:8][C:7]=2[C:15]2[C:16]3[NH:23][C:22]([CH3:24])=[C:21]([C:25]([OH:27])=[O:26])[C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Ethyl 4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate (example D.a19; 52.73 g; 131.4 mmol) is dissolved in tert. BuOH (500.0 mL) and water (5.0 mL). After addition of commercially available KOtBu (73.70 g; 656.8 mmol) the reaction mixture is stirred at 100° C. over night and cooled to ambient temperature. Water (1500 mL) is added and pH is adjusted to 6.0 by careful addition of 2M aqueous citric acid. The precipitated product is filtered washed with several portions of water and dried under reduced pressure to yield 45.3 g of the title compound as off-white solid.

Aufarbeitung

temperaturecooled to ambient temperature
filtrationThe precipitated product is filtered
washwashed with several portions of water
customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-41ea7a3af26e4ee1bc756fd0aa88219a
Quelldatensatz: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09376442B2

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