1,2-Dibromoethane → HCID 14035911, compound

HRID 1506572Notes

Reaction equation

HRID 1506572 reaction equation
[CH2:1]([NH:8][C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[NH:11][CH:12]=[N:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26]Br>CN(C=O)C>[CH2:1]([NH:8][C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[CH2:26][CH2:25][Br:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 62389N-Benzyl-1H-purin-6-amine

Product 1

HCID 14035911HCID 14035911, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Benzylaminopurine (1 g, 4.43 mmol), K2CO3 (2.45 g, 17.8 mmol) and 1,2-dibromoethane (1.15 mL, 13.3 mmol) was stirred for 16 h at room temperature under CaCl2 plug in DMF (30 mL). After removal of the DMF by vacuum evaporation, the resulting material was diluted with water (30 mL) and extracted into ethyl acetate (EtOAc) (3×15 mL). The organic fractions were combined, washed with water (2×10 mL), dried over Na2SO4, purified by carbofiltration and concentrated under vacuum. The pure product was purified by flash chromatography—chloroform:methanol (9:1) was used as an eluent. Yield: 82%.

Workup

  1. customAfter removal of the DMF
  2. customby vacuum evaporation
  3. additionthe resulting material was diluted with water (30 mL)
  4. extractionextracted into ethyl acetate (EtOAc) (3×15 mL)
  5. washwashed with water (2×10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationpurified by carbofiltration
  8. concentrationconcentrated under vacuum
  9. customThe pure product was purified by flash chromatography—chloroform:methanol (9:1)

Sources & evidence

ORD record
ord-46080dd3b9d04786b8daa4a6cf72b086
Source dataset
uspto-grants-2015_12
Patent number
US09220269B2

Reaction notes

Loading…