Water → 9-(2-bromoethyl)-9H-purin-2-amine

HRID 273279Notes

Reaction equation

HRID 273279 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12]O)=[CH:4][N:3]=1.C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCOCC1>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][Br:15])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 3443792-(2-Aminopurin-9-yl)ethanol

Product 1

HCID 114705279-(2-bromoethyl)-9H-purin-2-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

17.92 g (0.1 mole) of 2-amino-9-(2-hydroxyethyl)purine was completely dissolved in 200 ml of 1,4-dioxane. The solution was added with 49.75 g (0.15 mole) of carbon tetrabromide and cooled below 5° C. To the cooled material, 39.34 g (0.15 mole) of triphenylphosphine was added, followed by stirring for 5 hours at room temperature. After completion of the reaction, 300 ml of water was added to the reaction product, which was then extracted four times with 500 ml portions of a mixed solution of chloroform and methanol (4:1). The organic layer was collected, and dried with anhydrous magnesium sulfate, followed by filtration and washing. The resulting filtrate was concentrated under reduced pressure, and crystallized from chloroform, 15.74 g (65%) of white 2-amino-9-(2-bromoethyl)purine.

Workup

  1. temperaturecooled below 5° C
  2. additionwas added to the reaction product, which
  3. extractionwas then extracted four times with 500 ml portions of a mixed solution of chloroform and methanol (4:1)
  4. customThe organic layer was collected
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfollowed by filtration
  7. washwashing
  8. concentrationThe resulting filtrate was concentrated under reduced pressure
  9. customcrystallized from chloroform, 15.74 g (65%) of white 2-amino-9-(2-bromoethyl)purine

Sources & evidence

ORD record
ord-00d59afc0b2f4110a7b66535648b291a
Source dataset
uspto-grants-2008_11
Patent number
US07456282B2

Reaction notes

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