Water → 3-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1380430Notes

Reaction equation

HRID 1380430 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[O:4].[F:6][C:7]([F:14])([F:13])[C:8](=[CH2:12])[C:9](Cl)=[O:10].O>CN(C=O)C>[CH3:1][N:2]1[CH2:12][CH:8]([C:7]([F:14])([F:13])[F:6])[C:9](=[O:10])[NH:5][C:3]1=[O:4].[CH3:1][N:2]1[C:9](=[O:10])[CH:8]([C:7]([F:14])([F:13])[F:6])[CH2:12][NH:5][C:3]1=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 11719MethylureaHCID 101490162-(Trifluoromethyl)prop-2-enoyl chloride

Product 2

HCID 130049793-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 30%HCID 130049801-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methylurea (148 mg; 2.0 mmoles) in DMF (2 ml) was cooled to 0° C., and α-trifluoromethylacryloyl chloride (317 mg; 2.0 mmoles) was added dropwise. The mixture was stirred at room temperature for 1 hour, and water (20 ml) was added. The mixture was extracted with methylene chloride (20 ml×1, 10 ml×2). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by a column chromatography on silica gel (chloroform:ethyl acetate=3:1) to give 39 mg (yield: 10%) of 1-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-3) and 117 mg (yield: 30%) of 3-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-2).

Workup

  1. extractionThe mixture was extracted with methylene chloride (20 ml×1, 10 ml×2)
  2. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a column chromatography on silica gel (chloroform:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-cbc7d333692443de91618c2cf3611781
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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