Loxoribine → 6-Hydroxy-2-imino-9-pentofuranosyl-7-propyl-2,3,7,9-tetrahydro-8H-purin-8-one

HRID 846282Notes

Reaction equation

HRID 846282 reaction equation
[CH2:1]([N:4]1[C:21]2[C:20](=[O:22])[NH:19][C:18]([NH2:23])=[N:17][C:16]=2[N:6]([C@@H:7]2[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[C:5]1=[O:24])[CH:2]=[CH2:3]>[Pd].C(O)C>[CH2:1]([N:4]1[C:21]2[C:20](=[O:22])[NH:19][C:18]([NH2:23])=[N:17][C:16]=2[N:6]([C@@H:7]2[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[C:5]1=[O:24])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 135410906Loxoribine

Product 1

HCID 1354844556-Hydroxy-2-imino-9-pentofuranosyl-7-propyl-2,3,7,9-tetrahydro-8H-purin-8-oneYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-allyl-8-oxoguanosine (Example 8; 1.0 g, 2.9 mM) 10% Pd/C (100 mg) and ethanol (100 ml) was stirred at room temperature under an atmosphere of hydrogen for 3 hours. The catalyst was filtered through a pad of Celite and washed with ethanol (100 ml). The combined filtrate was concentrated in vacuo. The residue was dissolved in methanol (20 ml) and treated with ether (200 ml). The resulting solid was filtered and dried at 60° C. to provide the title compound in 55% yield as a white powder, mp 151°-153° C. NMR(DMSO-d6): δ 10.8(bs, 1H); 6.5(bs, 2H); 5.5(d J=5.5 Hz, 1H); 0.8(d, J=7 Hz, 3H). IR (KBr): 1680 and 1640 cm-1.

Workup

  1. filtrationThe catalyst was filtered through a pad of Celite
  2. washwashed with ethanol (100 ml)
  3. concentrationThe combined filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in methanol (20 ml)
  5. additiontreated with ether (200 ml)
  6. filtrationThe resulting solid was filtered
  7. customdried at 60° C.

Sources & evidence

ORD record
ord-7c56a4e82b40473a87520bbf9a9d8441
Source dataset
uspto-grants-1992_08
Patent number
US05136030

Reaction notes

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