Potassium Carbonate → HCID 18981017, compound

HRID 482440Notes

Reaction equation

HRID 482440 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[NH:11][C:10]2=[O:20])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:27]OS(C1C(C)=CC(C)=CC=1C)(=O)=O>O1CCCC1.O>[NH2:27][N:11]1[C:12]([C:16]([F:19])([F:17])[F:18])=[CH:13][C:14](=[O:15])[N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:10]1=[O:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 189810643-(4-Methoxyphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 18981017HCID 18981017, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.10 grams (0.0073 mole) of 3-(4-methoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (recovered from previous reactions) and 1.21 grams (0.0088 mole) of potassium carbonate in 30 mL of tetrahydrofuran was stirred for five minutes at ambient temperature and then 1.58 grams (0.0073 mole) of 1-aminooxysulfonyl-2,4,6-trimethylbenzene (prepared in a manner known by one skilled in the art) was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for three hours. At the conclusion of this period, the reaction mixture was diluted with water, and the resulting mixture was extracted with two 50 mL portions of ethyl acetate. The combined ethyl acetate extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 0.9 gram of crude product. This 0.90 grams of crude product was combined with 0.92 grams of crude product prepared by a similar route to yield a total of 1.82 grams of crude product. The 1.82 grams of crude product was purified by flash chromatography, yielding 1.5 grams of 1-amino-3-(4-methoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, m.p. 176°-178° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added
  2. additionUpon completion of addition
  3. extractionthe resulting mixture was extracted with two 50 mL portions of ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customyielding 0.9 gram of crude product
  8. customprepared by a similar route
  9. customto yield a total of 1.82 grams of crude product
  10. customThe 1.82 grams of crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-fdfbc173971248f4af1d510d83539429
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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