Acetone → 4-(2-Hydroxy-1-hexen-1-yl)-1-(2-O-methyl-3,5,-di-O-benzoyl-beta-D-ribofuranosyl)pyrimidin-2-one

HRID 2210633Notes

Reaction equation

HRID 2210633 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][N:10]([C@@H:13]2[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:17]([O:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:14]2[O:15][CH3:16])[C:9](=[O:39])[N:8]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].CC(C)=[O:42]>O.C(O)(=O)C>[OH:42][C:2]([CH2:3][CH2:4][CH2:5][CH3:6])=[CH:1][C:7]1[CH:12]=[CH:11][N:10]([C@@H:13]2[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:38])[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C@@H:17]([O:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:14]2[O:15][CH3:16])[C:9](=[O:39])[N:8]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 228567304-(1-Hexyn-1-yl)-1-(2-O-methyl-3,5,-di-O-benzoyl-beta-D-ribofuranosyl)pyrimidin-2-one

Product 1

HCID 1372265204-(2-Hydroxy-1-hexen-1-yl)-1-(2-O-methyl-3,5,-di-O-benzoyl-beta-D-ribofuranosyl)pyrimidin-2-oneYield 19%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-(1-Hexyn-1-yl)-1-(2-O-methyl-3,5,-di-O-benzoyl-β-D-ribofuranosyl)pyrimidin-2-one was dissolved in acetone (40 ml) and to this solution was added mercuric sulfate dissolved in H2O (10 ml) and acetic acid (10 ml). This solution was stirred at room temperature for 5 hours. The reaction was purified by silica gel column chromatography. Pooling of appropriate fractions and concentration gave 225 mg (19%) of the title compound.

Workup

  1. customThe reaction was purified by silica gel column chromatography
  2. concentrationPooling of appropriate fractions and concentration

Sources & evidence

ORD record
ord-32589ad1244f44d6898fe0bdc3ab8e0f
Source dataset
uspto-grants-1995_10
Patent number
US05459243

Reaction notes

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