Potassium Carbonate → HCID 86713559, Verbindung

HRID 2404010

Reaktionsgleichung

Reaktionsgleichung von HRID 2404010
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([O-:14])=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[NH2:15][C:16]1[C:21]([CH:22]=O)=[CH:20][N:19]=[C:18]([S:24][CH3:25])[N:17]=1.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2[C:12](=[O:14])[N:15]([CH3:26])[C:16]3[N:17]=[C:18]([S:24][CH3:25])[N:19]=[CH:20][C:21]=3[CH:22]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 69507942-(3,5-Dimethoxyphenyl)acetate

Produkt 1

HCID 86713559HCID 86713559, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-(3,5-dimethoxyphenyl)acetate (6) (440 mg, 2.40 mmol), 4-amino-2-(methylthio)pyrimidine-5-carbaldehyde (4) (605 mg, 2.88 mmol) and potassium carbonate (662 mg, 4.8 mmol) in DMF (30 mL) was stirred at 110° C. for 3 hours. The reaction was monitored by LCMS. The reaction mixture was diluted with H2O (30 mL), and extracted by EtOAc (3×40 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/EtOAc=2:1) to afford 6-(3,5-dimethoxyphenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (7) (683 mg, 83%) as a white solid. MS (ES+) C17H17N3O5S requires: 343. found: 344 [M+H]+.

Aufarbeitung

  1. extractionextracted by EtOAc (3×40 mL)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel, petroleum ether/EtOAc=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e481bef1260d4c82b55ca3dee258c021
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802697B2

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