Bromine → 2-(6-Amino-5-bromopyrimidin-4-yloxy)ethanol

HRID 2314Notes

Reaction equation

HRID 2314 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[CH:3]=1.[Br:12]Br>CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[C:3]=1[Br:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 189310692-((6-Aminopyrimidin-4-yl)oxy)ethanol

Product 1

HCID 189311062-(6-Amino-5-bromopyrimidin-4-yloxy)ethanolYield 104.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 2-(6-aminopyrimidin-4-yloxy)ethanol (400 mg) in methanol (4 ml) is added dropwise a solution of bromine (437 mg) in methanol (2 ml). The mixture is evaporated to remove the solvent, and the residue is dissolved in ethyl acetate. The mixture is treated with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate/tetrahydrofuran. The organic layer is washed, dried, and evaporated to remove the solvent to give 2-(6-amino-5-bromopyrimidin-4-yloxy)ethanol (632 mg).

Workup

  1. customThe mixture is evaporated
  2. customto remove the solvent
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. additionThe mixture is treated with saturated aqueous sodium hydrogen carbonate solution
  5. extractionextracted with ethyl acetate/tetrahydrofuran
  6. washThe organic layer is washed
  7. customdried
  8. customevaporated
  9. customto remove the solvent

Sources & evidence

ORD record
ord-2f3278729434431a9be2a0b527dc71ea
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Reaction notes

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