Potassium Carbonate → 5-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluoro-4-methylbenzenamine

HRID 450469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450469
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15](SC)[N:14]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[NH2:34][C:35]1[C:36]([F:43])=[CH:37][C:38]([CH3:42])=[C:39]([OH:41])[CH:40]=1.C([O-])([O-])=O.[K+].[K+]>ClCCl.CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([O:41][C:39]4[C:38]([CH3:42])=[CH:37][C:36]([F:43])=[C:35]([NH2:34])[CH:40]=4)[N:14]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 672523404-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

Produkt 1

HCID 673975355-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluoro-4-methylbenzenamineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine from Example A18 (200 mg, 0.64 mmol) in dichloromethane was added m-CPBA (220 mg, 1.28 mmol). The reaction was stirred for 2 hour at RT. Water was added, the organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organics were washed with brine and concentrated in vacuo. The residue was combined with 5-amino-4-fluoro-2-methylphenol (180 mg, 1.28 mmol) and K2CO3 (176 mg, 1.28 mmol) in DMF (5 mL) and the resultant mixture was heated at 90° C. overnight. After filtration and concentration, the residue was purified by silica gel column chromatography to give 5-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluoro-4-methylbenzenamine (210 mg, 84% yield). MS (ESI) m/z: 406.2 (M+H).

Aufarbeitung

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organics were washed with brine
  4. concentrationconcentrated in vacuo
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8da5559b86e64996abad71ecc26ee44e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486951B2

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