Potassium Carbonate → 3-chloro-4-((2,4-difluoro-3-methylbenzyl)oxy)-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one

HRID 2199523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2199523
[Cl:1][C:2]1[C:3](=[O:27])[N:4]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]([OH:26])([CH3:25])[CH3:24])[N:18]=3)[CH:11]=2)[C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[C:32]([CH3:37])[C:31]=1[F:38].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCCC>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[C:3](=[O:27])[N:4]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]([OH:26])([CH3:24])[CH3:25])[N:18]=3)[CH:11]=2)[C:5]([CH3:9])=[CH:6][C:7]=1[O:8][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[C:32]([CH3:37])[C:31]=1[F:38]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 21899848Ethylacetate heptaneHCID 866993063-chloro-4-hydroxy-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-oneHCID 866993081-(Bromomethyl)-2,4-difluoro-3-methylbenzene

Produkt 1

HCID 717690183-chloro-4-((2,4-difluoro-3-methylbenzyl)oxy)-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-oneAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2855718-Crown-6KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-chloro-4-hydroxy-2′-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5′,6-dimethyl-2H-[1,4′-bipyridin]-2-one (386 mg, 1.0 mmol) in N,N-dimethylformamide (1.7 mL) was added 1-(bromomethyl)-2,4-difluoro-3-methylbenzene (243 mg, 1.1 mmol), potassium carbonate (0.35 g, 2.52 mmol) and 18-crown-6 (7 mg). The slurry was stirred at ambient temperature for 18 hours. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The solution was concentrated in vacuo to provide a brown oil. Normal phase chromatography (ethyl acetate/heptane) provided 319 mg of the alkylated product: MS (M+H) 528.

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solution was concentrated in vacuo
  5. customto provide a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-f8d983b88d9241aca12e35df189b8673
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359300B2

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