Water → 5-(1-aminoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2369020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369020
[N:1]([CH:4]([C:6]1[CH:11]=[C:10]([N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:9]2[N:29]=[CH:30][C:31]([C:32]3[CH:33]=[N:34][C:35]4[C:40]([CH:41]=3)=[CH:39][C:38]([F:42])=[CH:37][CH:36]=4)=[C:8]2[N:7]=1)[CH3:5])=[N+]=[N-].C1COCC1.CP(C)C.O>CCOC(C)=O>[NH2:1][CH:4]([C:6]1[CH:11]=[C:10]([N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[N:9]2[N:29]=[CH:30][C:31]([C:32]3[CH:33]=[N:34][C:35]4[C:40]([CH:41]=3)=[CH:39][C:38]([F:42])=[CH:37][CH:36]=4)=[C:8]2[N:7]=1)[CH3:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 68983TrimethylphosphineHCID 86664796HCID 86664796, Verbindung

Produkt 1

HCID 665845645-(1-aminoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-(1-azidoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (6.2 g, 10.3 mmol) and THF (90 mL) was added 1M trimethylphosphine in THF (30.8 mL, 30.8 mmol) dropwise. After 30 minutes the reaction was complete by HPLC. Water (30 mL) was therefore added and the reaction stirred an additional hour. The contents of the flask were transferred to a separatory funnel, diluted with 300 mL of EtOAc and washed three times with water and three times with brine. The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Purified the remaining crude material by flash chromatography (0-2% 0.7N NH3 in MeOH/CHCl3) to afford 5-(1-aminoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (4.9 g, 82% yield) as a yellow solid. HPLC: 6.62 min (Method C). LCMS:ESI+ m/z of 583 (M+H)

Aufarbeitung

  1. customThe contents of the flask were transferred to a separatory funnel
  2. washwashed three times with water and three times with brine
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurified the remaining crude material by flash chromatography (0-2% 0.7N NH3 in MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-34d5981ed57d410eb1dbfdb892f6bf3d
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703784B2

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