N-Bromosuccinamide → 8-Bromo-1-methyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 2386642Notes

Reaction equation

HRID 2386642 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:3]1=[O:17].[Br:18]NC(=O)CCC(N)=O>CN(C=O)C>[Br:18][C:7]1[NH:8][C:9]2[C:10](=[O:11])[N:2]([CH3:1])[C:3](=[O:17])[N:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 248477161-methyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 592995728-Bromo-1-methyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dioneYield 12.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-methyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione (0.06 g, 0.25 mmol) was dissolved in DMF (2 ml) and N-bromosuccinamide (0.045 g, 0.25 mmol) added. The mixture was stirred for 18 h, concentrated and the crude purified by eluting through an aminopropyl SPE (5 g) with first methanol then 5% acetic acid/methanol to elute product. The product was further purified by mass directed auto prep to yield the title compound as a white solid (0.01 g, 12%). NMR δH (400 MHz, d6-DMSO) 0.86 (t, 3H, J=7 Hz), 1.21-1.35 (m, 4H), 1.59-1.68 (m, 2H), 3.22 (s, 3H), 3.91 (t, 2H, J=7.5 Hz), 14.39 (br. s, 1H); m/z 315, 317 [MH+].

Workup

  1. concentrationconcentrated
  2. customthe crude purified
  3. washby eluting through an aminopropyl SPE (5 g) with first methanol
  4. wash5% acetic acid/methanol to elute product
  5. customThe product was further purified by mass

Sources & evidence

ORD record
ord-b92275c192c24a899d38e1f2fb5ca5eb
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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