Ethylene Glycol → 2-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]ethan-1-ol

HRID 1398661Notes

Reaction equation

HRID 1398661 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.[CH2:22]([OH:25])[CH2:23][OH:24].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[NH2:20][C:16]1[N:15]=[C:14]([N:7]2[C:6]3[CH:21]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[O:24][CH2:23][CH2:22][OH:25])[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 10796Cesium carbonateHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 681816032-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]ethan-1-olYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (1 g, 2.45 mmol), ethane-1,2-diol (15 mL) and cesium carbonate (3 g, 9.18 mmol) was stirred overnight at room temperature and then diluted with 200 mL of water. The resulting solution was extracted with 2×200 mL of dichloromethane. The combined organic layers were washed with 3×200 mL of water, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 300 mg (34%) of 2-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]ethan-1-ol as a yellow solid. 1H NMR (300 MHz, DMSO) delta 8.39 (d, J=5.4 Hz, 1H), 8.30 (s, 1H), 7.51 (s, 2H), 7.09 (d, J=5.4 Hz, 1H), 4.78 (t, J=5.2 Hz, 2H), 4.08 (t, J=4.2 Hz, 2H); LC-MS: m/z=+350 (M+H)+.

Workup

  1. extractionThe resulting solution was extracted with 2×200 mL of dichloromethane
  2. washThe combined organic layers were washed with 3×200 mL of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-837aefbbe3bc4080ba9b3e377fdf4f48
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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