Trifluoroacetic anhydride → HCID 118599043, compound

HRID 1050403Notes

Reaction equation

HRID 1050403 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:16].OO.NC(N)=O>ClCCl>[Br:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N+:4]([O-:16])[CH:3]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 52987579Ethyl 5-bromopyrimidine-2-carboxylate

Product 1

HCID 118599043HCID 118599043, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. cooled solution of 1-ethyl 5-bromopyrimidine-2-carboxylate (2, 1.5 g, 6.5 mmol) in dichloromethane (30 mL), trifluoroacetic anhydride (13.69 g, 65 mmol) and Urea hydrogen peroxide (6.1 g, 65 mmol) were added. The reaction mixture was stirred at room temperature for 16 h. TLC showed consumption of starting material, the reaction mixture was diluted with water (10 mL) and neutralized with solid sodium bicarbonate. The solution was extracted with dichloromethane (2×40 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 5-bromo-2-(ethoxycarbonyl) pyrimidine 1-oxide (3) as yellow liquid which was used without further purification. Yield: 0.64 g, crude; MS (ESI) m/z 247.13 [M+1]+.

Workup

  1. additionwere added
  2. customconsumption of starting material
  3. additionthe reaction mixture was diluted with water (10 mL)
  4. extractionThe solution was extracted with dichloromethane (2×40 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72eee71ec5694fb5a2b7e1f581cde6b4
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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