Water → 3-(4,6-Dimethoxypyrimidine-2-yl)-2-methyl-7-metoxymethylindole

HRID 916734

Reaktionsgleichung

Reaktionsgleichung von HRID 916734
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12](=O)[CH3:13])[N:4]=1.[CH3:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24]N.C1(C)C=CC=CC=1.O>[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2[C:20]3[C:19](=[C:18]([CH2:17][O:16][CH3:15])[CH:23]=[CH:22][CH:21]=3)[NH:24][C:12]=2[CH3:13])[N:4]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 1140TolueneHCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-oneHCID 129793652-Methoxymethylphenylhydrazine

Produkt 1

HCID 115732153-(4,6-Dimethoxypyrimidine-2-yl)-2-methyl-7-metoxymethylindoleAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Into a reactor were fed 6.2 g (31.6 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone, 4.8 g (31.5 m moles) of 2-methoxymethylphenylhydrazine, 4.76 g (34.9 m moles) of zinc chloride and 60 ml of toluene. Refluxing was made for 2 hours with heating. After the completion of the reaction, the reaction mixture was cooled to room temperature. Water and ethyl acetate were added and phase separation was made. The ethyl acetate layer was concentrated. The resulting crystals were washed with diisopropyl ether to obtain 4.57 g (14.6 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methyl-7-metoxymethylindole. Yield: 46%

Aufarbeitung

  1. customInto a reactor were fed
  2. temperatureRefluxing
  3. temperaturewith heating
  4. customAfter the completion of the reaction
  5. customphase separation
  6. concentrationThe ethyl acetate layer was concentrated
  7. washThe resulting crystals were washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-addf75bc37514be49c805392e473df7f
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271263B2

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