Iodine → HCID 67241648, compound

HRID 19467Notes

Reaction equation

HRID 19467 reaction equation
[C@@H:1]1([C:10]2[C:11](=[O:16])[NH:12][CH:13]=[CH:14][CH:15]=2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[I:17]I.[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C@@H:1]1([C:10]2[C:11](=[O:16])[NH:12][CH:13]=[C:14]([I:17])[CH:15]=2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

6

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11831148HCID 11831148, compound

Product 1

HCID 67241648HCID 67241648, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

3-(β-D-Ribofuranosyl)-pyridin-2(1H)-one (342 mg, 1.5 mmol) (Matulic-Adamic, J., Beigelman, L., Tetrahedron Lett., 1997, 38, p. 203-206; Ishikawa, M., Hirao, I., Yokoyama, S., Tetrahedron Lett., 2000, 41, p. 3931-3934), iodine (573 mg, 2.3 mmol) and potassium iodide (KI) (657 mg, 7.9 mmol) were added to 50 mM sodium carbonate (36 ml) and heated at 110° C. for 12 hours. After the reaction, dichloromethane was added to separate the aqueous layer, followed by washing with dichloromethane. The aqueous layer was concentrated under reduced pressure and then purified by C18 reversed-phase HPLC to give 3-(β-D-ribofuranosyl)-5-iodopyridin-2(1H)-one (155 mg).

Workup

  1. additionwas added
  2. customto separate the aqueous layer
  3. washby washing with dichloromethane
  4. concentrationThe aqueous layer was concentrated under reduced pressure
  5. custompurified by C18 reversed-phase HPLC

Sources & evidence

ORD record
ord-7a3a135867b044a9ba36c50390620440
Source dataset
uspto-grants-2010_06
Patent number
US07745417B2

Reaction notes

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