Methanol → 7-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dione

HRID 2386601Notes

Reaction equation

HRID 2386601 reaction equation
[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[NH:8][C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].C1C(=O)N([Cl:22])C(=O)C1.CO>CN(C=O)C>[Cl:22][C:5]1[N:4]([CH2:1][CH:2]=[CH2:3])[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[NH:8][C:7]=2[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 31398ChlorosuccinimideHCID 598537957-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 592995327-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dioneYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione) (10.52 g, 54.7 mmol) in anhydrous DMF (60 ml) was added NCS (8.04 g, 60.2 mmol). The reaction mixture was left to stir under nitrogen at 20° C. for 6 hours. The reaction mixture was concentrated in vacuo to give an amber oil. MeOH was added and left to stand for 18 hours. The resulting residue was filtered and dried under vacuum to give the title compound (7.69 g, 62%). m/z 227.2 [MH+].

Workup

  1. waitThe reaction mixture was left
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give an amber oil
  4. waitleft
  5. waitto stand for 18 hours
  6. filtrationThe resulting residue was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f7bef0c033bb440aa19a32ad4c8a55ed
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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