Trifluoroacetic acid → Uracil Arabinoside

HRID 2361626Notes

Reaction equation

HRID 2361626 reaction equation
[CH:1]1[C:15](=[O:16])[N:14]=[C:13]2[N:3]([C@@H:4]3[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]3[O:12]2)[CH:2]=1.FC(F)(F)C(O)=[O:20]>CN(C)C=O>[C@@H:4]1([N:3]2[CH:2]=[CH:1][C:15](=[O:16])[NH:14][C:13]2=[O:12])[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]1[OH:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 8061382,2'-Anhydrouridine

Product 1

HCID 18323Uracil Arabinoside

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

500 mg (2.23 mmol) of the above product 2 is taken as the starting material to immerse in 5 mL of dimethyl formamide. 70 mL of trifluoroacetic acid (0.05N) is added with continuously stirring at 80° C. The solution is concentrated under reduced pressure by removing the residual part of the solution after the completion of the reaction, and then purified by rapid column chromatography (MeOH/CHCl3=1:3). A white powder product (1-(β-D-arabinofuranosyl)-pyrimidin-2,4(3H)-dione) 3 is obtained. Its weight and yield are 510 mg and 95% respectively.

Workup

  1. concentrationThe solution is concentrated under reduced pressure
  2. customby removing the residual part of the solution
  3. customafter the completion of the reaction
  4. custompurified by rapid column chromatography (MeOH/CHCl3=1:3)

Sources & evidence

ORD record
ord-30056213525b4137989057e8e558514c
Source dataset
uspto-grants-2014_04
Patent number
US08691789B2

Reaction notes

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