Potassium Carbonate → Methyl 3-[4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate

HRID 2172590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172590
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([OH:18])[N:13]=[C:12]2[CH3:19])[CH:5]=1.[F:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:23]=1[CH2:24]Br.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:24][C:23]3[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:22]=3[F:21])[N:13]=[C:12]2[CH3:19])[CH:5]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 1363878053-(4-hydroxy-2-methyl-6-oxo-6H-pyrimidin-1-yl)-4-methyl-benzoic acid methyl ester

Produkt 1

HCID 21089018Methyl 3-[4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoateAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of Intermediate 2 (500 mg, 1.82 mmol) in N,N-dimethylformamide (2 mL) was added 2,4-difluorobenzyl bromide (0.23 mL, 1.82 mmol), potassium carbonate (376 mg, 2.73 mmol) and 18-crown-6 (40 mg). The slurry was stirred at ambient temperature for one hour. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide the alkylated product as a white semi-solid (260 mg, 36% yield). MS (M+H): 401

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. filtrationThe slurry was filtered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-293d797cccb14002b479f1e58fb0c840
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056110B2

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