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Lithium Hydroxide → 3-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)benzoic acid

HRID 1014131
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1014131
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([O:27]C)=[O:26])[CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>CO.C1COCC1.O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([OH:27])=[O:26])[CH:16]=2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 57708324Methyl 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoate

Produkt 1

HCID 577083343-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)benzoic acidAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoate (0.3 g, 0.72 mmol) in methanol/THF (2/2, 4 mL) was added LiOH (0.122 g, 2.9 mmol) in H2O (4 mL) and the reaction mixture was stirred at rt for 2 h. It was concentrated under reduced pressure. the residue was diluted with water (2 mL) and was extracted with dichloromethane (5 mL). The aqueous layer was separated and was acidified with 1.5 N HCl (pH ˜5-6) to get a white precipitate, which was collected by filtration and dried under vacuum to give 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoic acid (0.2 g 69%) as a white solid.

Aufarbeitung

  1. concentrationIt was concentrated under reduced pressure
  2. additionthe residue was diluted with water (2 mL)
  3. extractionwas extracted with dichloromethane (5 mL)
  4. customThe aqueous layer was separated
  5. customto get a white precipitate, which
  6. filtrationwas collected by filtration
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f6543ca264e4479f8656d74975ffdc1d
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07982036B2

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