Chlorosuccinimide → 8-chloro-7-(4-chlorobenzyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200619Notes

Reaction equation

HRID 2200619 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12](=[O:17])[NH:11][C:10]=3[N:9]=[CH:8]2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:27])C(=O)C1>C1COCC1>[Cl:27][C:8]1[N:7]([CH2:6][C:5]2[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:15]2[C:14](=[O:16])[NH:13][C:12](=[O:17])[NH:11][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 904030007-[(4-Chlorophenyl)methyl]-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Product 1

HCID 904032898-chloro-7-(4-chlorobenzyl)-1H-purine-2,6(3H,7H)-dioneYield 18.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(4-chlorobenzyl)-1H-purine-2,6(3H,7H)-dione (2.2 g, 7.97 mmol) in THF (30 mL) was added NCS (1.1 g, 8.27 mmol) at 0° C. in portions. Then the resulting mixture was stirred at room temperature until it became a clear solution. The reaction was immediately quenched with ice-water and concentrated. The residue was extracted with ethyl acetate. The organic phase was washed with saturated sodium bicarbonate and brine, dried over sodium sulfate, and concentrated to give a crude product. This material was purified by silica gel chromatography eluting with DCM/methanol (50:1 to 20:1) to give 8-chloro-7-(4-chlorobenzyl)-1H-purine-2,6(3H,7H)-dione (450 mg, 18.2% yield) as white solid. LCMS retention time 1.071; LCMS MH+-58 311.

Workup

  1. customThe reaction was immediately quenched with ice-water
  2. concentrationconcentrated
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe organic phase was washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a crude product
  8. customThis material was purified by silica gel chromatography
  9. washeluting with DCM/methanol (50:1 to 20:1)

Sources & evidence

ORD record
ord-fdee6c47304943cca3bbcd00e20ef1ae
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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