Methanol → HCID 22807000, compound

HRID 1391078Notes

Reaction equation

HRID 1391078 reaction equation
[C:1]([C:3]1[C:11]2[C:10](Cl)=[N:9][C:8]([Cl:13])=[N:7][C:6]=2[N:5]([C@@H:14]2[O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]2[O:16]C(=O)C)[CH:4]=1)#[N:2].[CH3:32][OH:33]>C[O-].[Na+]>[Cl:13][C:8]1[N:9]=[C:10]([O:33][CH3:32])[C:11]2[C:3]([C:1]#[N:2])=[CH:4][N:5]([C@@H:14]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]3[OH:16])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 15403876HCID 15403876, compound

Product 1

HCID 22807000HCID 22807000, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

5-Cyano-2,4-dichloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (5, 400 mg) was dissolved in 40 ml of methanol containing 200 mg of sodium methoxide. The solution was stirred at room temperature for 1 hr and neutralized to pH 7 with Dowex 50W-X 12 (H30) resin. The resin was filtered and the solvent was evaporated to dryness in vacuo. The residue was dissolved in water, treated with decolorizing carbon, filtered and the product slowly crystallized under an air stream. The solid was recrystallized from ethanol-water to yield 100 mg of 7, mp 194-195°. The analytical sample was dried in an Abderhalden apparatus in vacuo for 2 hr. at 110° (mp unchanged).

Workup

  1. filtrationThe resin was filtered
  2. customthe solvent was evaporated to dryness in vacuo
  3. dissolutionThe residue was dissolved in water
  4. additiontreated with decolorizing carbon
  5. filtrationfiltered
  6. customthe product slowly crystallized under an air stream
  7. customThe solid was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-39f701888d654d98891cf1a596fdd442
Source dataset
uspto-grants-1979_02
Patent number
US04140851

Reaction notes

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