Propane, 1,1-diethoxy- → HCID 68378910, Verbindung

HRID 403497

Reaktionsgleichung

Reaktionsgleichung von HRID 403497
[N:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][C:9]2[C:10]([CH2:20][CH3:21])=[N:11][N:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH2:24]([O:26][CH:27]([O:30][CH2:31][CH3:32])[CH2:28][CH3:29])[CH3:25]>C(#N)C.CCOC(C)=O.[Cu]I>[CH2:24]([O:26][CH:27]([O:30][CH2:31][CH3:32])[C:28]1[N:3]=[N:2][N:1]([C:4]2[CH:23]=[CH:22][C:7]([CH2:8][C:9]3[C:10]([CH2:20][CH3:21])=[N:11][N:12]4[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[N:14][C:13]=34)=[CH:6][CH:5]=2)[CH:29]=1)[CH3:25]

Komponenten

6

Edukt 2

HCID 20858Propane, 1,1-diethoxy-HCID 86671756HCID 86671756, Verbindung

Produkt 1

HCID 68378910HCID 68378910, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-(4-azido-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine (20) (2 g, 6.53 mmol), propionaldehyde diethylacetal (1.294 g, 9.79 mmol) and copper(I) iodide (1.492 g, 7.83 mmol) in 33 ml of acetonitrile was stirred at r.t. for 24 h. The reaction was diluted in EtOAc and washed with sat aq Na2 CO3, water and brine. The organic layer was dried over anhydrous Na2 SO4, filtered and concentrated under HV. The crude product was purified by flash chromatography (silica gel, EtOAc/DCM 0% to 50%) to give a pale yellow oil.

Aufarbeitung

  1. washwashed
  2. customThe organic layer was dried over anhydrous Na2 SO4
  3. filtrationfiltered
  4. concentrationconcentrated under HV
  5. customThe crude product was purified by flash chromatography (silica gel, EtOAc/DCM 0% to 50%)
  6. customto give a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-e4fa77d7e9774dbaadf070dc482553ab
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748435B2

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