Sodium Acetate → Dimethyl (2-aminopurin-9-ylmethyl)succinate

HRID 1974842Notes

Reaction equation

HRID 1974842 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:13]([O:15][CH3:16])=[O:14])=[C:4](Cl)[N:3]=1.C([O-])(=O)C.[Na+]>[Pd].C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:13]([O:15][CH3:16])=[O:14])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 19027590Dimethyl 2-(2-amino-6-chloropurin-9-ylmethyl)succinate

Product 1

HCID 19027589Dimethyl (2-aminopurin-9-ylmethyl)succinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of dimethyl 2-(2-amino-6-chloropurin-9-ylmethyl)-succinate (3.28 g, 10 mmol), sodium acetate (1.5 g) and 5% palladium on charcoal (0.4 g) in ethanol (200 ml) was hydrogenated with agitation in a Parr apparatus at 40 psi for 115 h temperature. After filtration, sodium acetate (1.6 g) and 5% Pd/C (0.4 g) were added and the hydrogenation was continued for 70 h. After filtration and evaporation to dryness, the residue was extracted with 2×50 ml of chloroform and the combined extracts were evaporated to dryness affording 2.6 g (89%) of crude dechlorinated product.

Workup

  1. filtrationAfter filtration, sodium acetate (1.6 g) and 5% Pd/C (0.4 g)
  2. additionwere added
  3. waitthe hydrogenation was continued for 70 h
  4. filtrationAfter filtration and evaporation to dryness
  5. extractionthe residue was extracted with 2×50 ml of chloroform
  6. customthe combined extracts were evaporated to dryness
  7. customaffording 2.6 g (89%) of crude dechlorinated product

Sources & evidence

ORD record
ord-7052158ec7ac450198257cbc0018cb2c
Source dataset
uspto-grants-1994_02
Patent number
US05284837

Reaction notes

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