3-(Trifluoromethyl)aniline → 2-(3-trifluoromethylphenylamino)pyrimidin-4(3H)-one

HRID 1692991Notes

Reaction equation

HRID 1692991 reaction equation
CS[C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[F:10][C:11]([F:20])([F:19])[C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>COCCOCCOC>[F:10][C:11]([F:19])([F:20])[C:12]1[CH:13]=[C:14]([NH:15][C:3]2[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 798232-(Methylthio)-1H-pyrimidin-4-one

Product 1

HCID 14042422-(3-trifluoromethylphenylamino)pyrimidin-4(3H)-oneYield 21%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

To 2-(methyl-thio)pyrimidine-4(3H)-one, 1, (5 g, 35.21 mmol) in diglyme (25 mL) is added 3-trifluoromethylaniline (5.26 mL, 42.25 mmol). The resulting mixture is heated to reflux and stirred for 18 hours. A solid forms upon cooling the mixture to room temperature. The solid is washed with hexanes to afford 1.9 g (21% yield) of the desired compound. MS (ESI, pos. ion) m/z: 256 (M+1).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux
  3. washThe solid is washed with hexanes

Sources & evidence

ORD record
ord-3dce30d0751147ac847d7816ddcf22bf
Source dataset
uspto-grants-2012_04
Patent number
US08158641B2

Reaction notes

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