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

HRID 1398659Notes

Reaction equation

HRID 1398659 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 681815834-[6-bromo-2-(2,2,2-trifluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amineYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-897d690b7a8c427e834391a2131cae0c
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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