Potassium Carbonate → 8-(5-Bromothieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-ol

HRID 928598

Reaktionsgleichung

Reaktionsgleichung von HRID 928598
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.[CH:12]12[NH:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][CH:14]([OH:20])[CH2:13]2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C.ClCCl>[Br:1][C:2]1[C:10]2[C:9]([N:19]3[CH:12]4[CH2:18][CH2:17][CH:16]3[CH2:15][CH:14]([OH:20])[CH2:13]4)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 681478-Azabicyclo[3.2.1]octan-3-olHCID 454802995-Bromo-4-chlorothieno[2,3-d]pyrimidine

Produkt 1

HCID 895793758-(5-Bromothieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-olAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Bromo-4-chlorothieno[2,3-d]pyrimidine (2.11 g, 8.5 mmol) in dry acetonitrile (100 mL) was treated with 8-azabicyclo[3.2.1]octan3-ol (1.34 g, 10.6 mmol) and potassium carbonate (3.519 g, 25.5 mmol) and stirred and heated at reflux for 4 h. The reaction was diluted with ethyl acetate (200 mL) and dichloromethane (100 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulphate and concentrated in vacuum to give 8-(5-bromothieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-ol as a yellow solid (2.890 g, 8.5 mmol, 100%). This was used directly in the next step without further purification. 1H NMR (CDCl3) δ: 1.83 (2H, d, J=12 Hz), 2.0 (2H, br s) 2.28 (2H, d, J=6 Hz), 2.45 (2H, d, J=8 Hz), 4.15 (1H, br s), 4.7 (2H, br s), 7.35 (1H, s), 8.45 (1H, s).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. washwashed with water (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-abba901b65c746fe8b35cdf50c036085
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290511B2

Verknüpfte Notizen

Wird geladen…