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

HRID 1107652

Reaction equation

HRID 1107652 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 4.37N 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 50 H+ -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): δ 8.1 (d, 1 H, H6); 6.0 (d, 1 H, H5); 5.65 (m, 2 H, H1', 2'-OH); 5.25, 5.2 (d,t, 2 H, 3'-OH, 5'-OH); 2.45 (s, 3 H, 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-829f44f8778b43a28eeda208494df08f
Source dataset
uspto-grants-2000_05
Patent number
US06060592

Linked notes

Loading…