Ethyl Acetate → HCID 69518240, compound

HRID 855141Notes

Reaction equation

HRID 855141 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Cl[C:29]1[N:34]=[CH:33][C:32]([CH2:35][CH3:36])=[CH:31][N:30]=1.CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:29]1[N:34]=[CH:33][C:32]([CH2:35][CH3:36])=[CH:31][N:30]=1)[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 35727632-Chloro-5-ethylpyrimidineHCID 58934836HCID 58934836, compound

Product 1

HCID 69518240HCID 69518240, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of ethyl 6-chloro-7-hydroxyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.2g, 0.62 mmol) and potassium carbonate (342 mg, 2.48 mmol) in 3 mL of dry DMF was added a reagent of 2-chloro-5-ethylpyrimidine (450 uL, 3.72 mmol). The reaction was then heated at 130° C. for 51 hours. After cooling to room temperature, to the reaction was added 150 mL of EtOAc. The resulting organic phase was washed with brine, and dried over anhydrous magnesium sulfate. After removing the solvents, the residue was purified on a short silica gel column with EtOAc/Hexane to afford 260 mg of a brown oil, which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction
  2. washThe resulting organic phase was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the solvents
  5. customthe residue was purified on a short silica gel column with EtOAc/Hexane

Sources & evidence

ORD record
ord-5c45c057c1ef4dcba3c12f6f32d0774f
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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