HCID 57432834, compound → (2S,3S,4R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

HRID 744166Notes

Reaction equation

HRID 744166 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][CH:37]=[N:38][C:39]=2Cl)(=O)C1C=CC=CC=1.COCCOC.[NH3:50]>N.CO>[C@H:11]1([N:34]2[CH:42]=[N:41][C:40]3[C:35]2=[N:36][CH:37]=[N:38][C:39]=3[NH2:50])[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 57432834HCID 57432834, compoundHCID 86749850[(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(6-chloropurin-9-yl)oxolan-2-yl]methyl benzoate

Product 1

HCID 448374(2S,3S,4R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diolYield 67%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

A solution of 9 (1.00 g) in DME/NH3 (50 ml) was heated at 80° C. in a steel bomb for 24 hours. After cooling, the solvent was evaporated and the solid obtained was stirred in NH3 /MeOH (100 ml) overnight. After the evaporation of the solvent, the residue was dissolved in water (50 ml), washed with CHCl3 (2×25 ml) and ether (2×25 ml). The water layer was evaporated and the residue crystallized from water to give pure 10 (0.30 g, 67%) as white crystals: m.p. 225° C. (dec).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customthe solid obtained
  4. customAfter the evaporation of the solvent
  5. dissolutionthe residue was dissolved in water (50 ml)
  6. washwashed with CHCl3 (2×25 ml) and ether (2×25 ml)
  7. customThe water layer was evaporated
  8. customthe residue crystallized from water

Sources & evidence

ORD record
ord-e2a5092893a747d8a148475980ac4abc
Source dataset
uspto-grants-1996_09
Patent number
US05559101

Reaction notes

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