Water → HCID 86723835, compound

HRID 576733Notes

Reaction equation

HRID 576733 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][C:5](=O)[N:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:3]1=[O:20].O.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:5]1[N:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:3](=[O:20])[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=1

Participants

4

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 90251647HCID 90251647, compound

Product 1

HCID 86723835HCID 86723835, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 1-methyl-3-(3-(trifluoromethyl)phenyl)pyrimidin-2,4,6(1H, 3H, 5H)-trione (2.74 g) (prepared in Reference Example 55) in phosphorus oxychloride (22 ml) was added water (0.55 ml) slowly and the resulting mixture was stirred with heating under reflux for one hour. After concentration under reduced pressure, the reaction solutions were cooled to 0° C. and to the residue was added water (50 ml) slowly with stirring. The resulting mixture was extracted with ethyl acetate (50 ml×3), and the resulting extracts were dried and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 6-chloro-3-methyl-1-(3-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (1.54 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for one hour
  3. concentrationAfter concentration under reduced pressure
  4. additionwas added water (50 ml) slowly
  5. stirringwith stirring
  6. extractionThe resulting mixture was extracted with ethyl acetate (50 ml×3)
  7. customthe resulting extracts were dried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-92dd6730dd444e79843189cb38f5312e
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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