N-bromobutanimide → 2-benzylamino-8-bromo-9-ethyl-9H-purin-6-ylamine

HRID 457695Notes

Reaction equation

HRID 457695 reaction equation
[CH2:1]([NH:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[CH2:18][CH3:19])=[C:11]([NH2:20])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O>CN(C=O)C>[CH2:1]([NH:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[C:14]([Br:21])[N:15]2[CH2:18][CH3:19])=[C:11]([NH2:20])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11471166HCID 11471166, compound

Product 1

HCID 98630752-benzylamino-8-bromo-9-ethyl-9H-purin-6-ylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-benzylamino-9-ethyl-9H-purin-6-ylamine (1.0 mmol), a compound of formula (4), in 10 mL of dry DMF was added N-bromosuccinimide (267 mg, 1.5 mmol). The reaction mixture was stirred at room temperature for 1 hour. The solvent was then removed in vacuo and the residue partitioned between water and chloroform. The organic layer was washed with 1N sodium hydroxide, dried (Na2SO4), filtered, and the filtrate concentrated in vacuo. The residue was chromatographed on a silica gel column, eluting with chloroform/methanol; (98/2), to give 2-benzylamino-8-bromo-9-ethyl-9H-purin-6-ylamine as a chromatographically pure solid.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue partitioned between water and chloroform
  3. washThe organic layer was washed with 1N sodium hydroxide
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with chloroform/methanol

Sources & evidence

ORD record
ord-de809e1a6f4f49b19078eba5b834587e
Source dataset
uspto-grants-2007_03
Patent number
US07189730B2

Reaction notes

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