Water → 4-[6-Bromo-2-(oxetan-3-yloxy)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

HRID 1398649

Reaktionsgleichung

Reaktionsgleichung von HRID 1398649
[O:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[N:20]=[C:19](C(Cl)(Cl)Cl)[N:18]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH2:31])[N:26]=3)[C:17]=2[CH:32]=1.O>CN(C=O)C>[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[N:20]=[C:19]([O:5][CH:3]3[CH2:4][O:1][CH2:2]3)[N:18]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH2:31])[N:26]=3)[C:17]=2[CH:32]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 9942117Oxetan-3-ol2×HCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Produkt 1

HCID 681815884-[6-Bromo-2-(oxetan-3-yloxy)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of oxetan-3-ol (0.04 ml, 0.61 mmol) in DMF (5 ml) at 0° C. was added cesium carbonate (499.75 mg, 1.53 mmol) followed by 4-[6-bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine (250 mg, 0.61 mmol). The reaction was stirred at RT overnight, then re-charged with oxetan-3-ol (3 eq) and stirred for a total of 5 days at RT. Water was added (15 ml) to the combined reaction mixtures and the product extracted into DCM (2×30 ml). The combined organic extracts were washed with water and brine (10 ml each), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound; 1H NMR (500 MHz, DMSO) delta 4.83-4.70 (2H, m), 5.03-4.89 (2H, m), 5.85-5.75 (1H, m), 7.19-7.05 (3H, m), 7.51-7.34 (2H, m), 8.40 (1H, d, J=5.5 Hz), 8.45 (1H, d, J=1.7 Hz); LC-MS: m/z=+362/364 (M+H)+.

Aufarbeitung

  1. stirringstirred for a total of 5 days at RT
  2. customto the combined reaction mixtures
  3. extractionthe product extracted into DCM (2×30 ml)
  4. washThe combined organic extracts were washed with water and brine (10 ml each)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11cf07fbe473490cac598f86d6af7194
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901313B2

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