2-Fluoroethanol → 4-[2-(2-fluoroethoxy)-6-iodo-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

HRID 1398682Notes

Reaction equation

HRID 1398682 reaction equation
[I: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][CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[F:22][CH2:23][CH2:24][O:25][C:8]1[N:7]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=2)[C:6]2[CH:21]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=2[N:9]=1

Participants

6

Reactant 3

HCID 97372-FluoroethanolHCID 10796Cesium carbonateHCID 681819434-[6-iodo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 866696094-[2-(2-fluoroethoxy)-6-iodo-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amineYield 17.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[6-iodo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (1 g, 2.20 mmol), 2-fluoroethan-1-ol (900 mg, 14.05 mmol) and cesium carbonate (4.3 g, 13.20 mmol) in N,N-dimethylformamide (10 mL) was stirred for 14 hr at room temperature. The reaction mixture was diluted with 50 mL of ethyl acetate then washed with 5×10 mL of water. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column (ethyl acetate/petroleum ether, 10:1) to afford 150 mg (17%) of 4-[2-(2-fluoroethoxy)-6-iodo-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as brown oil: LC-MS: m/z=400 (M+H)+.

Workup

  1. washthen washed with 5×10 mL of water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on a silica gel column (ethyl acetate/petroleum ether, 10:1)

Sources & evidence

ORD record
ord-1282d28e986c460f9ec44bc0b75b9d28
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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