Benzyl Bromide → HCID 58126934, Verbindung

HRID 1971816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971816
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:15]([CH2:16][C:17](=[O:24])[N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:14]=[CH:13][N:8]2[C:9](=[O:12])[C:10]=1[OH:11])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:15]([CH2:16][C:17](=[O:24])[N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:14]=[CH:13][N:8]2[C:9](=[O:12])[C:10]=1[O:11][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 581269886-Hydroxy-5-oxo-1-(2-oxo-2-piperidin-1-yl-ethyl)-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester

Produkt 1

HCID 58126934HCID 58126934, VerbindungAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The crude product of example 2 was dissolved in DMF (50 ml) and then K2CO3 (3.3 g, 0.024 mol) was added. After stirring at room temperature for about 0.5 hours, benzyl bromide (4.0 g, 0.0234 mol) was added drop-wise. Then the mixture was heated at 80° C. for another 5 hours. After cooling to room temperature, the solids were filtered off and washed with ethyl acetate. The filtrate was diluted with EA, washed with water and then brine, dried and concentrated. The residue was purified by column chromatography (CH2Cl2/MeOH=50/1) to give the titled compound (2.0 g, 2-step yield 49.3%).

Aufarbeitung

  1. temperatureThen the mixture was heated at 80° C. for another 5 hours
  2. temperatureAfter cooling to room temperature
  3. filtrationthe solids were filtered off
  4. washwashed with ethyl acetate
  5. additionThe filtrate was diluted with EA
  6. washwashed with water
  7. dry with materialbrine, dried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (CH2Cl2/MeOH=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-f4a304265470460eb1494a1cdf2f4e59
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431581B2

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