Potassium Carbonate → 4-{[2-(Trifluoromethyl)-5-pyrimidinyl]oxy}benzaldehyde

HRID 705895Notes

Reaction equation

HRID 705895 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:20])([F:19])[C:12]1[N:17]=[CH:16][C:15]([OH:18])=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:20][C:11]([F:10])([F:19])[C:12]1[N:13]=[CH:14][C:15]([O:18][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:16][N:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 135906802-(Trifluoromethyl)pyrimidin-5-ol

Product 1

HCID 866231314-{[2-(Trifluoromethyl)-5-pyrimidinyl]oxy}benzaldehydeYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-fluorobenzaldehyde (0.196 mL, 1.828 mmol), 2-(trifluoromethyl)-5-pyrimidinol (300 mg, 1.828 mmol), and K2CO3 (505 mg, 3.66 mmol) in DMF (2 mL) was heated with a microwave reactor at 130° C. for 1 h. After removing the solvent, the residue was diluted with water, extracted with DCM. The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification via flash chromatography then afforded the title compound (351 mg, 1.309 mmol, 71.6% yield). LCMS: rt=2.97 min, [M+H+]=269

Workup

  1. customAfter removing the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash chromatography

Sources & evidence

ORD record
ord-988c6d60acf141939749f09acc7258e4
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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