Sodium Methoxide → 2-Methyl-1-(-beta-D-ribofuranosyl)pyrimidin-4-one
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]=1Participants
4
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
- customevaporated
- customThe residue was partitioned between water (100 ml) and dichloromethane (2×150 ml)
- customevaporated
- 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
Reaction notes
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