Adenosine → 2-Amino-9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

HRID 1682086Notes

Reaction equation

HRID 1682086 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@@H:12]2[F:19])=[C:4](N)[N:3]=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:23]>O>[F:19][C@H:12]1[C@H:13]([OH:14])[C@@H:15]([CH2:17][OH:18])[O:16][C@H:11]1[N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:23])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

4

Reactant 2

HCID 60961AdenosineHCID 460081(2R,3R,4S,5R)-5-(2,6-diaminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol

Product 1

HCID 1354349402-Amino-9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-Diamino-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine (0.1 g, 0.35 mmoles) prepared as in Example 1, was dissolved in 10 ml of water. Calf intestine adenosine deaminase (10 I.U., Boehringer Mannheim) was added and the solution incubated at 37° C. for one day. The solvent was removed under vacuum. The residue was dissolved in acetonitrile/water (85/15) and chromatographed on silica gel with acetonitrile/water (85/15) as the solvent. Product containing fractions were combined and the solvent removed under vacuum. The residue was dissolved in water and lyophilization yielded 0.14 g of the title compound that analysed as a 1.1 hydrate.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in acetonitrile/water (85/15)
  3. customchromatographed on silica gel with acetonitrile/water (85/15) as the solvent
  4. additionProduct containing fractions
  5. customthe solvent removed under vacuum
  6. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-6a40a82f62af4dc1b7d291e61a3686bd
Source dataset
uspto-grants-1992_12
Patent number
US05175274

Reaction notes

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