HCID 70195631, compound → 9-(4-Hydroxybutyl)guanine

HRID 2288226Notes

Reaction equation

HRID 2288226 reaction equation
[Br-].C([O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:18][N:17](CC2C=CC=CC=2)[C:16]2[C:15](=[O:26])[NH2+:14][C:13]([NH:27]C(=O)C)=[N:12][C:11]1=2)(=O)C>[Pd].CO>[OH:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:18]=[N:17][C:16]2[C:15](=[O:26])[NH:14][C:13]([NH2:27])=[N:12][C:11]1=2

Participants

4

Reactant 1

HCID 70195631HCID 70195631, compound

Product 1

HCID 1354334109-(4-Hydroxybutyl)guanineYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

9-(4-Acetoxybutyl)-N2 -acetyl-7-benzylguaninium bromide (39.7 g; content 97.5%; 80.8 mmol) was added to a mixed solution of methanol (404 ml) and 7.48 g (1.62 mmol) of 5% Pd/C (water content 54%). The reaction was carried out at 50° C. for 4 h under hydrogen atmosphere (1 atm). After completion of the reaction (confirmed by HPLC), the reaction mixture was filtered through Celite, and the solvent was removed by distillation under reduced pressure. Then, water (130 ml) and 25% NaOH (45.2 g) were added to the residue and stirred overnight at 40° C. The mixture was neutralized by 2N HCl stirred at room temperature for 2 h. The precipitated crystals were filtered and dried at 50° C. under reduced pressure for a yield of 17.33 g of 9-hydroxybutylguanine (97.2% purity, 93.4% yield).

Workup

  1. customAfter completion of the reaction (confirmed by HPLC)
  2. filtrationthe reaction mixture was filtered through Celite
  3. customthe solvent was removed by distillation under reduced pressure
  4. additionThen, water (130 ml) and 25% NaOH (45.2 g) were added to the residue
  5. stirringstirred at room temperature for 2 h
  6. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-8b4ed48308f94415b213ac3eb46475ed
Source dataset
uspto-grants-2000_07
Patent number
US06087497

Reaction notes

Loading…