Lithium Hydroxide → 4-(4-Hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid

HRID 605351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605351
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[C:6]([NH:18][C:19]2[C:20]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[N:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH:5]=1.[Li+].[OH-]>C1COCC1>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([S:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][C:6]=2[NH:18][C:19]2[C:20]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[N:25][C:21]=3[N:22]=[CH:23][N:24]=2)=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 3939Lithium Hydroxide2×HCID 670402984-(4-Hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester

Produkt 1

HCID 670409154-(4-Hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acidAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 4-(4-hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester (0.50 g, 1.1 mmol) in THF (5 mL) was added aqueous LiOH [prepared from LiOH monohydrate (0.15 g) and H2O (1.5 mL)] dropwise at room temperature. The mixture was stirred at room temperature for 24 hours. Additional aqueous LiOH [prepared from LiOH monohydrate (0.15 g) and H2O (1.5 mL)] was added at room temperature. The mixture was mixture was stirred at room temperature for 23 hours, and then evaporated. The aqueous mixture was diluted with 50 mL of H2O, washed with AcOEt, and treated with active charcoal. The mixture was filtered and the filtrate was carefully acidified to pH 4-5 with 10% HCl under stirring. The resulting solid was collected by filtration, washed with H2O, and dried at 40° C. for 3 days under reduced pressure to give the title compound as pale yellow crystal (0.35 g, 73%). 1H-NMR (300 MHz, DMSO-d6) δ ppm: 1.33 (d, J=7.0 Hz, 6H), 3.22 (septet, J=7.0 Hz, 1H), 6.81-6.90 (m, 1H), 6.85 (d, J=8.5 Hz, 2H), 7.30 (d, J=8.5 Hz, 2H), 7.63 (br-d, J=8.4 Hz, 1H), 7.73 (br-d, J=8.1 Hz, 1H), 7.85 (br-s, 1H), 8.57 (s, 1H), 8.86 (d, J=8.4 Hz, 1H), 10.14 (s, 1H).

Aufarbeitung

  1. stirringwas stirred at room temperature for 23 hours
  2. customevaporated
  3. additionThe aqueous mixture was diluted with 50 mL of H2O
  4. washwashed with AcOEt
  5. additiontreated with active charcoal
  6. filtrationThe mixture was filtered
  7. stirringunder stirring
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with H2O
  10. customdried at 40° C. for 3 days under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-990980f6bb5b4948bd235a6f5ec2a99c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910595B2

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