N,N'-Dimethylurea → 1,3-Dimethyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1380414Notes

Reaction equation

HRID 1380414 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4](O)=[O:5].[CH3:10][NH:11][C:12]([NH:14][CH3:15])=[O:13]>CN(C)C=O>[CH3:10][N:11]1[CH2:7][CH:3]([C:2]([F:9])([F:8])[F:1])[C:4](=[O:5])[N:14]([CH3:15])[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 7293N,N'-DimethylureaHCID 5876942-(Trifluoromethyl)acrylic acid

Product 1

HCID 130049781,3-Dimethyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of α-trifluoromethylacrylic acid (700 mg; 5.0 mmoles) and 1,3-dimethylurea (441 mg; 5.0 mmoles) in dimethylformamide (DMF) (3 ml) was heated at 90° C. with stirring for 28 hours. DMF was evaporated under reduced pressure, and the residue was purified by a column chromatography on silicagel (chloroform) to give 861 mg (yield: 82%) of 1,3-dimethyl-5-trifluoromethyl-5,6-dihydrouracil (OF-1).

Workup

  1. customDMF was evaporated under reduced pressure
  2. customthe residue was purified by a column chromatography on silicagel (chloroform)

Sources & evidence

ORD record
ord-34ec29c6bdca4416a60e79461faa2260
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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