Potassium Carbonate → (R)-3-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl]-pentanoic acid methyl ester

HRID 1887196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887196
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C@H:5]([N:8]1[C:13](=[O:14])[C:12]2[N:15]=[CH:16][CH:17]=[CH:18][C:11]=2[NH:10][C:9]1=[O:19])[CH2:6][CH3:7].[I-].C[N+](C)(C)[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][C:30]([CH3:35])=[CH:31][C:32]=2[CH3:34])[N:27]([CH3:36])[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C@H:5]([N:8]1[C:13](=[O:14])[C:12]2[N:15]=[CH:16][CH:17]=[CH:18][C:11]=2[N:10]([CH2:24][C:25]2[C:33]3[C:28](=[CH:29][C:30]([CH3:35])=[CH:31][C:32]=3[CH3:34])[N:27]([CH3:36])[CH:26]=2)[C:9]1=[O:19])[CH2:6][CH3:7]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 67502941HCID 67502941, VerbindungHCID 86664592HCID 86664592, Verbindung

Produkt 1

HCID 67501927(R)-3-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl]-pentanoic acid methyl esterAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 1.75 g of (R)-3-(2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl)-pentanoic acid methyl ester, 2.5 g of trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-ammonium iodide and 1.7 g of potassium carbonate in 50 mL of N,N-dimethylformamide is heated at 65° C. for 3 h. The resulting mixture is diluted with water and the product is extracted with ethyl acetate. The organic layer is washed with brine, dried (sodium sulfate) filtered and concentrated. The residue is purified by flash chromatography on silica gel to give 1.0 g (35%) of (R)-3-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl]-pentanoic acid methyl ester.

Aufarbeitung

  1. extractionthe product is extracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-92931ce10ad049a293cc2b54f75d0809
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501749B2

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