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

HRID 1380427Notes

Reaction equation

HRID 1380427 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]([NH2:14])=[O:13].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH3:10][N:11]1[CH2:7][CH:3]([C:2]([F:9])([F:8])[F:1])[C:4](=[O:5])[NH:14][C:12]1=[O:13].[CH3:10][N:11]1[C:4](=[O:5])[CH:3]([C:2]([F:9])([F:8])[F:1])[CH2:7][NH:14][C:12]1=[O:13]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11719MethylureaHCID 5876942-(Trifluoromethyl)acrylic acid

Product 2

HCID 130049793-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 15%HCID 130049801-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of α-trifluoromethylacrylic acid (700 mg; 5.0 mmoles) and methylurea (378 mg; 5.1 mmoles) in DMF (5 ml) was cooled to 0° C., and a solution of DCC (1.07 g; 5.2 mmoles) in DMF (3 ml) was added dropwise. The mixture was stirred for 1 hour, and the precipitated solid was filtered off and washed with ethyl acetate. DMF was evaporated under reduced pressure from the combined filtrates. The residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:3) to give 420 mg (yield: 43%) of 1-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-3) and 30 mg (yield: 15%) of 3-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-2).

Workup

  1. filtrationthe precipitated solid was filtered off
  2. washwashed with ethyl acetate
  3. customDMF was evaporated under reduced pressure from the combined filtrates
  4. customThe residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:3)

Sources & evidence

ORD record
ord-c1f37abc2c874542af83cb9e038ba8b1
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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