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

HRID 1398687Notes

Reaction equation

HRID 1398687 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][CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([O:25][CH2:24][CH2:23][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

6

Reactant 3

HCID 97372-FluoroethanolHCID 10796Cesium carbonateHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 866696134-[6-bromo-2-(2-fluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amineYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (500 mg, 1.23 mmol), 2-fluoroethan-1-ol (236 mg, 3.68 mmol) and cesium carbonate (1.2 g, 3.68 mmol) in N,N-dimethylformamide (3 mL) was stirred in a 20-mL sealed tube under nitrogen overnight at room temperature. The reaction mixture was diluted with 30 mL of water and the precipitate was collected by filtration to give 340 mg (79%) of 4-[6-bromo-2-(2-fluoroethoxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a yellow solid; LC-MS: m/z=+352 (M+H)+.

Workup

  1. customsealed tube under nitrogen overnight at room temperature
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-1d9f71cbf251438e96e913e039262f2d
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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