Trifluoroacetic anhydride → HCID 118598640, compound

HRID 1050404Notes

Reaction equation

HRID 1050404 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N+:6]([O-])[CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:17]>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:17])[NH:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 118599043HCID 118599043, compound

Product 1

HCID 118598640HCID 118598640, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a 0° C. cooled solution of 5-bromo-2-(ethoxycarbonyl)pyrimidine 1-oxide (3, 0.62 g, 2.5 mmol) in dimethylformamide (6 mL), trifluoroacetic anhydride (3.1 g, 15 mmol) was added dropwise. The reaction mixture was heated at 50° C. for 18 h. TLC showed consumption of starting material and solvent was removed under reduced pressure. The residue was triturated with methanol (2 mL) and filtered. The solid was washed with diethyl ether and dried under reduced pressure to afford ethyl 5-bromo-6-oxo-1,6-dihydropyrimidine-2-carboxylate (4) as off white solid. Yield: 0.21 g, 34%; MS (ESI) m/z 245.09 [M−1]−.

Workup

  1. additionwas added dropwise
  2. customconsumption of starting material and solvent
  3. customwas removed under reduced pressure
  4. customThe residue was triturated with methanol (2 mL)
  5. filtrationfiltered
  6. washThe solid was washed with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd5cab4f752846e0be421896c13218c7
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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