Hydrochloric Acid → 3-(4-Methoxyphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione

HRID 482439Notes

Reaction equation

HRID 482439 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[NH2:12]/[C:13](/[C:20]([F:23])([F:22])[F:21])=[CH:14]\[C:15](OCC)=[O:16].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:15](=[O:16])[CH:14]=[C:13]([C:20]([F:23])([F:22])[F:21])[NH:12][C:10]2=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 794431-Isocyanato-4-methoxybenzeneHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonate

Product 1

HCID 189810643-(4-Methoxyphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dioneYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 6.0 grams (0.0268 mole) of 4-methoxyphenyl isocyanate, 5.16 grams (0.028 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate, and 4.45 grams (0.032 mole) of potassium carbonate in 40 mL of N,N-dimethylformamide was heated to 140° C. where it stirred for one hour. After this time, the reaction mixture was poured into 100 mL of 10% aqueous hydrochloric acid. The resulting mixture was stirred for ten minutes and then extracted with three 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 to yield a black solid. This black solid was purified by flash chromatography, yielding 4.51 grams of 3-(4-methoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione. The NMR spectrum was consistent with the proposed structure.

Workup

  1. stirringThe resulting mixture was stirred for ten minutes
  2. extractionextracted with three 50 mL portions of ethyl acetate
  3. dry with materialThe combined ethyl acetate extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto yield a black solid
  7. customThis black solid was purified by flash chromatography

Sources & evidence

ORD record
ord-676d0b3c48014df0b0a777ba1824a5dd
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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