Acetone → 2-Amino-9-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-9H-purine bis hydrochloride

HRID 37086Notes

Reaction equation

HRID 37086 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])=[CH:4][N:3]=1.C(O)(C)C.[ClH:24].CC(C)=O>CO>[ClH:24].[ClH:24].[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])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 10355712(2R,3R,4R,5R)-5-(2-Amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol

Product 1

HCID 867486882-Amino-9-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-9H-purine bis hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (300 mg 1.11 mmol) in MeOH (20 ml) was added isopropanol (2.5 ml) previously saturated with hydrochloride (HCL) gas. Acetone (15 ml) was added and the solution evaporated to almost dryness under vacuum at room temperature. Trituration with ethyl acetate (15 ml) produced a white solid which was filtered and washed with ether.

Workup

  1. customthe solution evaporated to almost dryness under vacuum at room temperature
  2. customTrituration with ethyl acetate (15 ml) produced a white solid which
  3. filtrationwas filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-28097341039e4cbe8dc7d52b6100e3d6
Source dataset
uspto-grants-1995_05
Patent number
US05420115

Reaction notes

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