8-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione → 8-(8-Oxa-bicyclo[3.2.1]oct-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 395891Notes

Reaction equation

HRID 395891 reaction equation
[CH:1]12[O:8][CH:5]([CH:6]=[CH:7]1)[CH2:4][CH:3]([C:9]1[NH:17][C:16]3[C:15](=[O:18])[N:14]([CH2:19][CH2:20][CH3:21])[C:13](=[O:22])[N:12]([CH2:23][CH2:24][CH3:25])[C:11]=3[N:10]=1)[CH2:2]2>CO.[Pd]>[CH:5]12[O:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][CH:3]([C:9]1[NH:17][C:16]3[C:15](=[O:18])[N:14]([CH2:19][CH2:20][CH3:21])[C:13](=[O:22])[N:12]([CH2:23][CH2:24][CH3:25])[C:11]=3[N:10]=1)[CH2:4]2

Participants

4

Reactant 1

HCID 102911968-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

Product 1

HCID 181730868-(8-Oxa-bicyclo[3.2.1]oct-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (Example 50) (0.029 mmol, 0.010 g) in MeOH (5 ml) was added 10% Pd/C (50% H2O) and the resulting suspension stirred briskly under H2 (1 atm) for 2 h. The mixture was filtered through Celite and the cake rinsed with MeOH. Filtration and evaporation followed by purification by PLC, eluting with 1:1 EtOAc/CH2Cl2, provided the title compound (0.010 g, 100%). 1H NMR (100 MHz, CDCl3): 0.93-0.99 (m, 6H), 1.68-1.89 (m, 8H), 2.04-2.07 (m, 2H), 2.16-2.25 (m, 2H), 3.34-3.42 (m, 1H), 4.05-4.12 (m, 4H), 4.50 (br s, 2H), 8.9 (br s, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe cake rinsed with MeOH
  3. filtrationFiltration and evaporation
  4. customfollowed by purification by PLC
  5. washeluting with 1:1 EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-08c966b120a44a4e9c9d7e2cb583dc69
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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