Uridine → 2,2'-Anhydrouridine

HRID 2361625Notes

Reaction equation

HRID 2361625 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1O.C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:16]1[C:14](=[O:15])[N:13]=[C:11]2[N:10]([C@@H:1]3[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@@H:2]3[O:12]2)[CH:17]=1

Participants

5

Reactant 3

HCID 6029UridineHCID 7597Diphenyl carbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 8061382,2'-Anhydrouridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

500 mg (2.05 mmol) of uridine 1, 570 mg of (2.65 mmol, 1.3 gram-equivalent (eq)) of diphenyl carbonate, and 10 mg (0.12 mmol, 0.059 eq) of sodium bicarbonate are dissolved in 1 mL of dimethyl formamide and heated to 140° C. After the starting materials are completely consumed, the solution is cooled down to room temperature to form white precipitates. The white precipitates are washed by ice formic acid. Residual part of the solution is removed at reduced pressure. After collection, a white powder product (2,2′-cyclouridine) 2 is obtained. Its weight and yield are 370 mg and 80%, respectively.

Workup

  1. customAfter the starting materials are completely consumed
  2. temperaturethe solution is cooled down to room temperature
  3. customto form white precipitates
  4. customThe white precipitates
  5. washare washed by ice formic acid
  6. customResidual part of the solution is removed at reduced pressure
  7. customAfter collection

Sources & evidence

ORD record
ord-c27f9a9848d24e35a110c869ea3815ec
Source dataset
uspto-grants-2014_04
Patent number
US08691789B2

Reaction notes

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