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

HRID 1380419Notes

Reaction equation

HRID 1380419 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][C:17]([CH:19]([C:26]([F:29])([F:28])[F:27])[CH2:20][NH:21][C:22]([NH:24][CH3:25])=[O:23])=O>CN(C=O)C>[CH3:25][N:24]1[C:17](=[O:16])[CH:19]([C:26]([F:29])([F:28])[F:27])[CH2:20][NH:21][C:22]1=[O:23]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 133137911-(2-Hydroxycarbonyl-3,3,3-trifluoropropyl)-3-methylurea

Product 1

HCID 130049793-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of DCC (428 mg; 2.1 mmoles) in DMF (1 ml) was added dropwise to a solution of 1-(2-hydroxycarbonyl-3,3,3-trifluoropropyl)-3-methylurea (428 mg; 2.0 mmoles) obtained above in DMF (2 ml). The mixture was stirred for 1 hour, and the precipitated solid was filtered off and washed with ethyl acetate. The solvents were evaporated under reduced pressure from the combined filtrates. The residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:1) to give 368 mg (yield: 94%) of 3-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-2).

Workup

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

Sources & evidence

ORD record
ord-bbd2ecfa404748ed8c51d65b861ce89c
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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