1-Bromo-2-Chloroethane → 9-(2-Chloroethyl)-2,6-diamino-purine

HRID 1920664Notes

Reaction equation

HRID 1920664 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][Cl:21]>CN(C=O)C>[Cl:21][CH2:20][CH2:19][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[NH2:11]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 309762,6-Diaminopurine

Product 1

HCID 668680839-(2-Chloroethyl)-2,6-diamino-purineYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g (66.6 mmol) 2,6-diaminopurine were suspended under argon in 300 ml DMF and 21.6 g (156.5 mmol) potassium carbonate and 24 ml 1-bromo-2-chloroethane were added. The mixture was stirred for 64 hours at room temperature. The light yellow suspension was filtered and the solids were washed with 30 ml DMF and subsequently triturated with 100 ml water for 30 minutes. The mixture was filtered and the solids were washed with 50 ml water and dried in vacuo to give 10.15 g (72%) of the desired product as a white solid.

Workup

  1. filtrationThe light yellow suspension was filtered
  2. washthe solids were washed with 30 ml DMF
  3. customsubsequently triturated with 100 ml water for 30 minutes
  4. filtrationThe mixture was filtered
  5. washthe solids were washed with 50 ml water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-879382b092194ee892b0db0e9cbe463d
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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