Reaction #2267065

ord-612187d51ba74addb6bf4bbb1d079fac

Reaction equation

Cc1ccccc1
toluene
Cc1ccccc1
toluene
CS(C)=O
Dimethyl sulfoxide
Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
5-azacytidine
Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
5-azacytidine
CS(C)=O
DMSO
→
CS(C)=O.Cc1ccccc1
DMSO Toluene

Reactants

Cc1ccccc1
toluene
Cc1ccccc1
toluene
CS(C)=O
Dimethyl sulfoxide
Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
5-azacytidine
Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1
5-azacytidine
CS(C)=O
DMSO
—
resultant solution

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherpreheated to approximately 90° C., in separate 100-mL beakers
  2. 2
    workup.DISSOLUTIONto dissolve to a clear solution
  3. 3
    Otherpreheated to approximately 50° C.
  4. 4
    workup.ADDITIONwas added to the solution
  5. 5
    FiltrationThe product was collected by vacuum filtration as white crystals
  6. 6
    Otherto air dry

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06887855B2uspto-grants-2005_05