Ethyl Acetate → HCID 49780776, compound

HRID 1408474Notes

Reaction equation

HRID 1408474 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[F:11][C:12]([F:22])([F:21])[O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(OCC)(=O)C>C1COCC1>[Cl:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([NH:18][C:17]2[CH:19]=[CH:20][C:14]([O:13][C:12]([F:11])([F:21])[F:22])=[CH:15][CH:16]=2)[N:3]=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 6008484-(Trifluoromethoxy)anilineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 49780776HCID 49780776, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-Dichloro-pyrimidine-5-carbaldehyde (3.06 g, 17.5 mmol) in THF (15 mL) was added 4-trifluoromethoxyaniline (3.09 g, 17.45 mmol) at 0° C. The mixture was stirred for 2 h and ethyl acetate (100 mL) was added. The organic layer was separated from brine, dried (Na2SO4) and concentrated to yield crude title compound as yellow solids. The compound was then purified by silica gel column chromatography to give the title compound as yellow crystals. (2.9 g, 55%). MS m/z 318.2 (M+1).

Workup

  1. customThe organic layer was separated from brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto yield crude title compound as yellow solids
  5. customThe compound was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2caabc5bbef8482f96b118a4efea47ff
Source dataset
uspto-grants-2014_12
Patent number
US08921336B2

Reaction notes

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