Dimethyl Sulfoxide → Dimethylsulfoxide toluene

HRID 716623Notes

Reaction equation

HRID 716623 reaction equation
[CH3:1][S:2]([CH3:4])=[O:3].[C@@H]1(N2C=NC(N)=NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:1][S:2]([CH3:4])=[O:3].[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 1140Toluene2×HCID 9444Azacytidine2×

Product 1

HCID 22340214Dimethylsulfoxide toluene

Procedure

Dimethyl sulfoxide (DMSO) was used as the primary solvent to solubilize Form I of 5-azacytidine and toluene was used as the co-solvent as follows. Approximately 250 mg of 5-azacytidine was dissolved with approximately 5 mL of DMSO, preheated to approximately 90° C., in separate 100-mL beakers. The solids were allowed to dissolve to a clear solution. Approximately 45 mL of toluene, preheated to approximately 50° C., was added to the solution and the resultant solution was mixed. The solution was covered and allowed to equilibrate at ambient conditions. The product was collected by vacuum filtration as white crystals using a Buchner funnel. The collected product was allowed to air dry.

Workup

  1. custompreheated to approximately 90° C., in separate 100-mL beakers
  2. dissolutionto dissolve to a clear solution
  3. custompreheated to approximately 50° C.
  4. additionwas added to the solution
  5. filtrationThe product was collected by vacuum filtration as white crystals
  6. customto air dry

Sources & evidence

ORD record
ord-b074d01c4e4d41c9a15499d4882c8223
Source dataset
uspto-grants-2015_11
Patent number
US09192620B2

Reaction notes

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