Sodium Methoxide → HCID 69423353, compound

HRID 916603Notes

Reaction equation

HRID 916603 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:30]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[C:29]([CH3:40])[N:28]=[C:27]([CH3:41])[N:26]=1)(=O)C.C[O-].[Na+]>CO>[C@@H:6]1([O:24][C:25]2[C:30]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[C:29]([CH3:40])[N:28]=[C:27]([CH3:41])[N:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69421997HCID 69421997, compound

Product 1

HCID 69423353HCID 69423353, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-5-(4-methoxybenzyl)-2,6-dimethylpyrimidine (0.24 g) in methanol (4 mL) was added sodium methoxide (28% solution in methanol, 0.040 mL), and the mixture was stirred for 50 minutes at room temperature. After the reaction mixture was concentrated under reduced pressure, the residue was purified by column chromatography on silica gel (eluent: dichloro-methane/methanol=7/1) to give 4-(β-D-glucopyranosyloxy)-5-(4-methoxybenzyl)-2,6-dimethylpyrimidine (0.11 g).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: dichloro-methane/methanol=7/1)

Sources & evidence

ORD record
ord-cbf79a7b66d14f788b6034ef790690d8
Source dataset
uspto-grants-2007_09
Patent number
US07271153B2

Reaction notes

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