Hydrochloric Acid → HCID 18663752, compound

HRID 1956743Notes

Reaction equation

HRID 1956743 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[NH:8][C:7](=[O:9])[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:5](=[O:19])[CH:4]=1.[C:22](=O)([O-])[O-].[K+].[K+].CI.Cl>CN(C)C=O>[CH3:22][N:8]1[C:3]([C:2]([F:1])([F:20])[F:21])=[CH:4][C:5](=[O:19])[N:6]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[C:7]1=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18663753HCID 18663753, compound

Product 1

HCID 18663752HCID 18663752, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.0 grams (0.01 mole) of 6-trifluoromethyl-3-(4-methoxy-phenylmethyl)-2,4(1H,3H)-pyrimidinedione in 25 mL of N,N-dimethylform-amide was stirred and 1.4 grams (excess) of potassium carbonate was added. To this was then added 0.7 mL (0.01 mole) of methyl iodide. Upon completion of the addition the reaction mixture was stirred at ambient temperature for about 18 hours, then poured into a mixture of 100 mL of ice and 100 mL of aqueous 10% hydrochloric acid. The resultant solid was collected by filtration and washed with water. The solid was then dissolved in 200 mL of ethyl acetate and dried with magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure, yielding 2.1 grams (66.9% yield) of 1-methyl-6-trifluoromethyl-3-(4-methoxyphenylmethyl)-2,4(1H,3H)-pyrimidinedione, mp 79°-80° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. filtrationThe resultant solid was collected by filtration
  3. washwashed with water
  4. dissolutionThe solid was then dissolved in 200 mL of ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-82ca7a92474c499d9d180fc85fe14b8b
Source dataset
uspto-grants-1998_07
Patent number
US05780630

Reaction notes

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