1-Bromo-2-Chloroethane → HCID 11404234, compound

HRID 1162983Notes

Reaction equation

HRID 1162983 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[N:3]=1.Br[CH2:19][CH2:20][Cl:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:19][CH2:20][Cl:21])=[C:4]([NH:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[N:3]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 15366662HCID 15366662, compound

Product 1

HCID 11404234HCID 11404234, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-cyclohexylamino-purine (4 mmol), 1-bromo-2-chloroethane (8 mmol) and potassium carbonate (8 mmol, water free) in DMF (20 ml) are heated up to 45° C. and the mixture is stirred at this temperature for 5 hours. After cooling to RT the mixture is poured on water and extracted 3 times with ethyl acetate. The combined organic phases are washed twice with brine and the extract is dried over sodium sulfate and evaporated. The residue is dissolved in diethylether and pentane is added. The solid material formed is filtered of and dried (vacuum). A white powder with mp. 150-152° C., Rf=0.17 (CH2Cl2/MeOH=20:1) is obtained.

Workup

  1. additionis poured on water
  2. extractionextracted 3 times with ethyl acetate
  3. washThe combined organic phases are washed twice with brine
  4. dry with materialthe extract is dried over sodium sulfate
  5. customevaporated
  6. dissolutionThe residue is dissolved in diethylether
  7. additionpentane is added
  8. customThe solid material formed
  9. filtrationis filtered of and
  10. customdried (vacuum)
  11. customA white powder with mp. 150-152° C., Rf=0.17 (CH2Cl2/MeOH=20:1) is obtained

Sources & evidence

ORD record
ord-609a68004f324151b6f3dea9d4c5c994
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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