2,2,2-Trifluoroethanol → 4-[6-bromo-2-(2,2,2-trifluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

HRID 1398659

Reaktionsgleichung

Reaktionsgleichung von HRID 1398659
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8](C(Cl)(Cl)Cl)[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1.[F:22][C:23]([F:27])([F:26])[CH2:24][OH:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([O:25][CH2:24][C:23]([F:27])([F:26])[F:22])[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1

Komponenten

5

Edukt 3

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Produkt 1

HCID 681815834-[6-bromo-2-(2,2,2-trifluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amineAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (500 mg, 1.23 mmol), 2,2,2-trifluoroethan-1-ol (500 mg, 5.00 mmol) and cesium carbonate (2.5 g, 7.67 mmol) in N,N-dimethylformamide (5 mL) placed in a 10-mL sealed tube maintained under nitrogen was irradiated with microwave radiation at 70° C. for 2 hr. The residue was purified on a C18 column (acetonitrile/water, 5:95-80:20) to yield 260 mg (46%) of 4-[6-bromo-2-(2,2,2-trifluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a yellow solid. LC-MS: m/z=+388 (M+H)+.

Aufarbeitung

  1. customsealed tube
  2. temperaturemaintained under nitrogen
  3. customwas irradiated with microwave radiation at 70° C. for 2 hr
  4. customThe residue was purified on a C18 column (acetonitrile/water, 5:95-80:20)

Quellen und Nachweise

ORD-Eintrag
ord-897d690b7a8c427e834391a2131cae0c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901313B2

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