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

HRID 273278Notes

Reaction equation

HRID 273278 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.[Br:14]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.[OH-].[Na+]>C(#N)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][Br:14])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70579Triphenylphosphine dibromideHCID 3443792-(2-Aminopurin-9-yl)ethanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
35 °C

Procedure

17.92 g (0.1 mole) of 2-amino-9-(2-hydroxyethyl)purine was completely dissolved in 400 ml of acetonitrile, to which 84.42 g (0.20 mole) of dibromotriphenylphosphine was then added. The mixture was stirred for 5 hours at a temperature of 30-40° C. After completion of the reaction, 300 ml of water was added to the reaction product. The resulting solution was neutralized with aqueous sodium hydroxide solution and 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, 22.03 g (91%) of white 2-amino-9-(2-bromoethyl)purine.

Workup

  1. additionwas then added
  2. additionwas added to the reaction product
  3. extractionextracted 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, 22.03 g (91%) of white 2-amino-9-(2-bromoethyl)purine

Sources & evidence

ORD record
ord-0d278cd7c841464aa025a74a5ec384a6
Source dataset
uspto-grants-2008_11
Patent number
US07456282B2

Reaction notes

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