Lithium hydroxide, monohydrate → Lithium 2-(4-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoro-methyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetate

HRID 1473134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473134
O[Li:2].O.C([O:6][C:7](=[O:47])[CH2:8][C:9]1[C:10]([CH2:15][CH2:16][C:17]2[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=[C:19]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]4[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]4)=[CH:30][CH:29]=3)[N:18]=2)=[N:11][CH:12]=[N:13][CH:14]=1)C>C1COCC1.O.CO>[C:43]([O:42][C:40]([N:37]1[CH2:36][CH2:35][CH:34]([C:31]2[CH:30]=[CH:29][C:28]([NH:27][C:19]3[N:18]=[C:17]([CH2:16][CH2:15][C:10]4[C:9]([CH2:8][C:7]([O-:47])=[O:6])=[CH:14][N:13]=[CH:12][N:11]=4)[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=3)=[CH:33][CH:32]=2)[CH2:39][CH2:38]1)=[O:41])([CH3:46])([CH3:44])[CH3:45].[Li+:2]

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 71209322tert-Butyl 4-(4-((4-(2-(5-(2-ethoxy-2-oxoethyl)pyrimidin-4-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Produkt 1

HCID 71209343Lithium 2-(4-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoro-methyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetateAusbeute 103,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LiOH.H2O (0.020 g, 0.468 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(5-(2-ethoxy-2-oxoethyl)pyrimidin-4-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (I112) (0.096 g, 0.156 mmol) in THF (7 mL), water (1.5 mL) and methanol (1 mL) and the resulting mixture was allowed to stir at room temperature for 18 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (70 mL) and 2 M aqueous NaOH (80 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×70 mL), the combined organics were washed with brine (70 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (I113) (0.096 g, quantitative) as a pale yellow solid. LCMS Method C: rt 6.19 min; m/z 587.1 [M+H]+.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. additionthe residue was diluted with EtOAc (70 mL) and 2 M aqueous NaOH (80 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×70 mL)
  5. washthe combined organics were washed with brine (70 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-464b15f14aa641feb3417ddc2e7cea19
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012461B2

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