Potassium Carbonate → HCID 22347996, compound

HRID 897261Notes

Reaction equation

HRID 897261 reaction equation
C([N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:16])[CH:12]=2)[NH:7][C:6]1=[O:17])(C)(C)C.O([CH2:26][C:27]([F:30])([F:29])[F:28])S(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:26][C:27]([F:30])([F:29])[F:28])[C:6](=[O:17])[NH:5][C:14]2=[O:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 223480083-tert-Butyl-6-chloro-1H-quinazoline-2,4-dione

Product 1

HCID 22347996HCID 22347996, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-tert-butyl-6-chloro-1H-quinazoline-2,4-dione (1.0 g, 3.97 mmol) in acetonitrile (40 mL) was added trifluoroethyl triflate (0.736 mL, 4.76 mmol) and potassium carbonate (821 mg, 5.95 mmol). The reaction was heated to 50° C. and stirred 48 hrs. The solution was cooled, concentrated, and dissolved in ethyl acetate. The solution was washed with sodium bicarbonate, brine, dried over Na2SO4, filtered, and concentrated. The crude residue was dissolved in acetic acid and treated with 4 mL HBr solution (30 weight % in AcOH). The reaction was stirred for 3 hours at room temperature, and concentrated to provide 1.1 g of yellow solid. 1H NMR (300 MHz, CD3OD) δ ppm 4.96 (q, J=8.7 Hz, 2H), 7.53 (d, J=9.0 Hz, 1H), 7.75 (dd, J=2.6, 9.1 Hz, 1H), 8.07 (d, J=2.7 Hz, 1H); MS (ESI+Q1MS) m/z 279 [M+H]+

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate
  4. washThe solution was washed with sodium bicarbonate, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe crude residue was dissolved in acetic acid
  9. additiontreated with 4 mL HBr solution (30 weight % in AcOH)
  10. stirringThe reaction was stirred for 3 hours at room temperature
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-cf5fbb5c24904e6ab321bf7f83105e4e
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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