Ammonium formate → Famciclovir

HRID 5866

Reaction equation

HRID 5866 reaction equation
[C:1]([O:4][CH2:5][CH:6]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH2:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][C:12]([NH2:19])=[N:13][C:14]=2Cl)(=[O:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:4][CH2:5][CH:6]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH2:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][C:12]([NH2:19])=[N:13][CH:14]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 101551646-Chloro famciclovir

Product 1

HCID 3324FamciclovirYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine (0.36 g, 1.0 mmol) and 10% palladium-on-charcoal (30 mg) in methanol containing ammonium formate (400 mM, 10 ml) was heated under reflux for 30 minutes. The mixture was allowed to cool, filtered and the solvent removed. The residue was taken up in water and the solution extracted twice with chloroform. The organic layers were combined, dried (magnesium sulphate) and the solvent removed to afford 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine (0.29 g, 90%). Recrystallisation from ethyl acetate-hexane gave white shiny plates (0.25 g, 78%) m.p. 102°-104° C.; λmax (MeOH) 222 (27,500), 244 (4,890), and 309 (7,160) nm; νmax (KBr) 3340, 3170, 1745, 1730, 1660, 1615 and 1580 cm-1 ; δH (CDCl3) 1.90-2.05 (3H, m, 2'-H and 3' -H), 2.07 (6H, s, 2×CH3), 4.15 (4H, d, J 5.2 Hz, 2×4'-H), 4.21 (2H, t, J 7.2 Hz, 1'-H), 5.16 (2H, br s, 2-NH2), 7.79 (1H, s, 8-H), and 8.70 (1H, s, 6-H); (Found: C, 52.10; H, 6.00; N, 21.49%. C14H19N5O4 requires C, 52.33; H, 5.96; N, 21.79%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent removed
  6. extractionthe solution extracted twice with chloroform
  7. dry with materialdried (magnesium sulphate)
  8. customthe solvent removed

Sources & evidence

ORD record
ord-4433a99e49994b5fbc65a69fbcc99e86
Source dataset
uspto-grants-1993_09
Patent number
US05246937

Linked notes

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