Chlorosuccinimide → 3-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

HRID 1097639Notes

Reaction equation

HRID 1097639 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[CH:11][N:10]([CH2:14][CH:15]=[CH2:16])[C:9]=2[C:8](=[O:17])[NH:7][C:6]1=[O:18])[CH2:2][CH2:3][CH3:4].C1C(=O)N([Cl:26])C(=O)C1>CN(C=O)C>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:26])[N:10]([CH2:14][CH:15]=[CH2:16])[C:9]=2[C:8](=[O:17])[NH:7][C:6]1=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 592995893-butyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 592995823-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-butyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (3.34 g, 13.4 mmol) in anhydrous DMF (19 ml) was added NCS (1.97 g, 14.8 mmol) and left to stir at rt under nitrogen for 22 h. The mixture was concentrated in vacuo to give a yellow solid which was filtered and washed with MeOH to provide a first crop. The filtrate was concentrated to a solid and washed with MeOH to provide a second crop and repeated a further two occasions to provide the title compound. On the final wash the filtrate was further purified by SPE (Si, 20 g) cartridge eluting with EtOAc:cyclohexane (1:1). The combined solids were dried under vacuum to afford the title compound (2.42 g, 64%).

Workup

  1. waitleft
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a yellow solid which
  4. filtrationwas filtered
  5. washwashed with MeOH
  6. customto provide a first crop
  7. concentrationThe filtrate was concentrated to a solid
  8. washwashed with MeOH
  9. customto provide a second crop

Sources & evidence

ORD record
ord-fc005dd3880e4a71aa4e709631c30cbe
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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