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

HRID 2386608Notes

Reaction equation

HRID 2386608 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-dioneYield 64%

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 hours. The mixture was concentrated in vacuo to give a yellow solid which was filtered and washed with methanol. The filtrate was concentrated and the process repeated. On the final wash the filtrate was purified by SPE (Si, 20 g) cartridge eluting with 1:1; EtOAc:cyclohexane. The combined solids were dried under vacuum to afford the title compound (2.42 g, 64%); m/z 283.3 [MH+]

Workup

  1. waitleft
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a yellow solid which
  4. filtrationwas filtered
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated
  7. washOn the final wash the filtrate
  8. customwas purified by SPE (Si, 20 g) cartridge
  9. washeluting with 1:1
  10. customThe combined solids were dried under vacuum

Sources & evidence

ORD record
ord-d556e82ec3044461969e66f9c2e3f1f6
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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