Sodium Methoxide → HCID 86597448, compound

HRID 402314Notes

Reaction equation

HRID 402314 reaction equation
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@H:11]1[N:34]1[C:38]2=[CH:39][N:40]=[N:41][C:42](=[O:43])[C:37]2=[N:36][CH2:35]1)(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[C@@H:11]1([N:34]2[C:38]3=[CH:39][N:40]=[N:41][C:42](=[O:43])[C:37]3=[N:36][CH2:35]2)[O:12][C@H:13]([CH2:24][OH:25])[C@@H:14]([OH:15])[C@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86597447HCID 86597447, compound

Product 1

HCID 86597448HCID 86597448, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

1-(2,3,5-tri-O-Benzoyl-β-D-ribofuranosyl)imidazo[4,5-d]pyridazin-4-one (555 mg, 0.9 mmol) was added to a solution of sodium methylate (205 mg) in methanol (25 mL) and stirred at 20° C. for 2 hours. The reaction mixture was evaporated to dryness. The residue was dissolved in water and washed with ethyl acetate. The aqueous layer was concentrated under pressure. The crude product was purified on silica gel reverse-phase (C18) using water as eluant to give the title compound (220 mg) as a white powder.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionThe residue was dissolved in water
  3. washwashed with ethyl acetate
  4. concentrationThe aqueous layer was concentrated under pressure
  5. customThe crude product was purified on silica gel reverse-phase (C18)

Sources & evidence

ORD record
ord-8f0e0a04668048ffb856ed2b086b3f9d
Source dataset
uspto-grants-2014_06
Patent number
US08742101B2

Reaction notes

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