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

HRID 1380429Notes

Reaction equation

HRID 1380429 reaction equation
[CH3:1][NH:2][C:3]([NH:5][CH3:6])=[O:4].[F:7][C:8]([F:15])([F:14])[C:9](=[CH2:13])[C:10](Cl)=[O:11].O>CN(C=O)C>[CH3:1][N:2]1[CH2:13][CH:9]([C:8]([F:15])([F:14])[F:7])[C:10](=[O:11])[N:5]([CH3:6])[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 7293N,N'-DimethylureaHCID 101490162-(Trifluoromethyl)prop-2-enoyl chloride

Product 1

HCID 130049781,3-Dimethyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3-dimethylurea (423 mg; 4.8 mmoles) in DMF (5 ml) was cooled to 0° C., and α-trifluoromethylacryloyl chloride (792 mg; 5.0 mmoles) was added dropwise. The mixture was stirred at room temperature for 1 hour. Then, water (20 ml) was added, and the mixture was extracted with methylene chloride (20 ml×1, 10 ml×2). The combined extracts were dried over anhhdrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by a column chromatography on silica gel (chloroform) to give 508 mg (yield: 50%) of 1,3-dimethyl-5-trifluoromethyl-5,6-dihydrouracil (OF-1).

Workup

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

Sources & evidence

ORD record
ord-99914eaa805a428497f03c776a160626
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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