Trifluoromethanesulfonic acid → 5-Phenyluracil

HRID 1486534Notes

Reaction equation

HRID 1486534 reaction equation
C([N:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](=[O:26])[NH:16][C:15]1=[O:27])(C1C=CC=CC=1)C1C=CC=CC=1.OS(C(F)(F)F)(=O)=O>C(O)(C(F)(F)F)=O>[C:20]1([C:18]2[C:17](=[O:26])[NH:16][C:15](=[O:27])[NH:14][CH:19]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 90017824HCID 90017824, compound

Product 1

HCID 2871105-Phenyluracil

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

1-Benzhydryl-5-phenyl-pyrimidine-2,4-dione (0.13 g, 0.35 mmol) was added to solution of triflic acid (0.09 mL, 0.99 mmol) in TFA (0.87 mL) cooled to 0° C. The reaction mixture was stirred for 2 hrs and then quenched by addition of ice. The white precipitate was filtered and dried. The filtrate was diluted with EtOAc and the two phases were separated. The aqueous layer was further extracted with EtOAc (3×15 mL), the combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was taken up with a 1:1 dichloromethane/diethyl ether mixture; the product precipitated as white solid that was filtered and combined to the first fraction isolated (0.06 g, 65%). Analytical data were consistent with those reported in the literature (J. Org. Chem. 1990, 55, 1396-1399); 1H NMR (400 MHz, DMSO-d6) δ 7.25-7.30 (m 1H), 7.32-7.39 (m, 2H), 7.51-7.56 (m 2H), 7.60 (s 1H), 11.10 (br s, 1H), 11.22 (br s, 1H). MS (ESI) m/z: 187 [M-H]−.

Workup

  1. customquenched by addition of ice
  2. filtrationThe white precipitate was filtered
  3. customdried
  4. additionThe filtrate was diluted with EtOAc
  5. customthe two phases were separated
  6. extractionThe aqueous layer was further extracted with EtOAc (3×15 mL)
  7. dry with materialthe combined organic phases were dried over Na2SO4
  8. customthe solvent was removed under reduced pressure
  9. customthe product precipitated as white solid
  10. filtrationthat was filtered
  11. customisolated (0.06 g, 65%)

Sources & evidence

ORD record
ord-e77651e3c3ff490fadd964fa1b924ca0
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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