HCID 22807003, compound → HCID 22807002, compound

HRID 1391076Notes

Reaction equation

HRID 1391076 reaction equation
[C:1]([C:3]1[C:11]2[C:10](=[O:12])[N:9]([OH:13])[CH:8]=[N:7][C:6]=2[N:5]([C@@H:14]2[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:15]2[OH:16])[CH:4]=1)#[N:2]>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[C:1]([C:3]1[C:11]2[C:10](=[O:12])[N:9]([OH:13])[CH:8]=[N:7][C:6]=2[N:5]([C@@H:14]2[O:20][C@H:19]([CH2:21][O:22][C:17](=[O:18])[CH3:19])[C@@H:17]([O:18][C:15](=[O:16])[CH3:14])[C@H:15]2[O:16][C:10](=[O:12])[CH3:11])[CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 22807003HCID 22807003, compound

Product 1

HCID 22807002HCID 22807002, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

5-Cyano-3-N-hydroxy-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-one was dissolved in a mixture of 50 ml of pyridine and 25 ml of acetic anhydride. The solution was allowed to stand at room temperature for 5 hr and evaporated in vacuo to a thick oil. This residue was triturated with 100 ml of ethanol and the mixture was evaporated in vacuo to a solid foam which was again triturated with 100 ml of ethanol and evaporated in vacuo to dryness. The resulting foam was heated at reflux temperature with 100 ml of methanol for 1 hr. The methanol was removed in vacuo and an additional 100 ml of methanol was added and removed in vacuo to furnish a solid foam which was used without further purification.

Workup

  1. customevaporated in vacuo to a thick oil
  2. customThis residue was triturated with 100 ml of ethanol
  3. customthe mixture was evaporated in vacuo to a solid foam which
  4. customwas again triturated with 100 ml of ethanol
  5. customevaporated in vacuo to dryness
  6. temperatureThe resulting foam was heated
  7. temperatureat reflux temperature with 100 ml of methanol for 1 hr
  8. customThe methanol was removed in vacuo
  9. additionan additional 100 ml of methanol was added
  10. customremoved in vacuo
  11. customto furnish a solid foam which
  12. customwas used without further purification

Sources & evidence

ORD record
ord-7374a095ec2a47159f98ee581c572a7d
Source dataset
uspto-grants-1979_02
Patent number
US04140851

Reaction notes

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