Hydrochloric Acid → HCID 86723834, compound

HRID 576734Notes

Reaction equation

HRID 576734 reaction equation
Cl[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[N:5]([CH3:19])[C:4](=[O:20])[CH:3]=1.Cl.O1CC[CH2:24][CH2:23]1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C[CH2-].C[CH2-].[Zn+2]>[CH2:23]([C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[N:5]([CH3:19])[C:4](=[O:20])[CH:3]=1)[CH3:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 86723835HCID 86723835, compound

Product 1

HCID 86723834HCID 86723834, compound

Reagents, catalysts & solvents 2

HCID 11185557-20-0CatalystHCID 178418851HCID 178418851, compoundCatalyst

Procedure

To a solution of 6-chloro-3-methyl-1-(3-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (prepared in Reference Example 56) (1.12 g) in THF (tetrahydrofuran) (30 ml) were added under nitrogen atmosphere bis(tri-tert-butyl phosphine)palladium (188 mg) and zinc diethyl (1.1 M hexane solution, 10 ml) and the resulting mixture was stirred at room temperature for twenty minutes. The reaction solutions were added into 1 N (normality) of hydrochloric acid and the resulting mixture was extracted with ethyl acetate (50 ml×2). The organic layer was washed with saturated saline (50 ml), dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 6-ethyl-3-methyl-1-(3-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (0.94 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (50 ml×2)
  2. washThe organic layer was washed with saturated saline (50 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-002c91e9ca3c45a584b608fa9a8cc242
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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