Sodium Methoxide → 2-Methyl-1-(-beta-D-ribofuranosyl)pyrimidin-4-one

HRID 840612

Reaction equation

HRID 840612 reaction equation
[CH3:1][C:2]1[N:3]([C@@H:9]2[O:31][C@H:30]([CH2:32][O:33]C(=O)C3C=CC=CC=3)[C@@H:20]([O:21]C(=O)C3C=CC=CC=3)[C@H:10]2[O:11]C(=O)C2C=CC=CC=2)[CH:4]=[CH:5][C:6](=[O:8])[N:7]=1.C[O-].[Na+]>CO>[CH3:1][C:2]1[N:3]([C@@H:9]2[O:31][C@H:30]([CH2:32][OH:33])[C@@H:20]([OH:21])[C@H:10]2[OH:11])[CH:4]=[CH:5][C:6](=[O:8])[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 120421992-Methyl-1-(2',3'5'-tri-o-benzoyl-beta-d-ribofuranosyl)-pyrimidin-4-one

Product 1

HCID 103994612-Methyl-1-(-beta-D-ribofuranosyl)pyrimidin-4-oneYield 39.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-methyl-1-(2′,3′5′-tri-O-benzoyl-β-D-ribofuranosyl)-pyrimidin-4-one (13.86 g, 25 mmol) in methanol (150 ml) was added 4.37 N sodium methoxide solution in MeOH (2.5 mmol, 0.1 eq.). The solution was stirred overnight at room temperature and then evaporated. The residue was partitioned between water (100 ml) and dichloromethane (2×150 ml). The aqueous layer was neutralized with Dowex 50H+-form and evaporated. The orange oily residue was crystallized from ethanol/acetone 3:1 to give the title compound (2.37 g, 39%). 1H-NMR (CDCl3): δ8.1 (d, 1H, H6); 6.0 (d, 1H, H5); 5.65 (m, 2H, H1′, 2′-OH); 5.25, 5.2 (d,t, 2H, 3′-OH, 5′-OH); 2.45 (s, 3H, CH3)

Workup

  1. customevaporated
  2. customThe residue was partitioned between water (100 ml) and dichloromethane (2×150 ml)
  3. customevaporated
  4. customThe orange oily residue was crystallized from ethanol/acetone 3:1

Sources & evidence

ORD record
ord-edcfc51c5e7f4bbeb2cc3d831f08d8a0
Source dataset
uspto-grants-2002_04
Patent number
US06369040B1

Linked notes

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