Water → Methyl 4-(3-formyl-4-methoxy-2-methylphenyl)pyrimidine-2-carboxylate

HRID 873546Notes

Reaction equation

HRID 873546 reaction equation
C(N(CC)CC)C.Cl[C:9]1[N:14]=[C:13]([C:15]2[C:16]([CH3:25])=[C:17]([C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH:18]=[O:19])[CH:12]=[CH:11][N:10]=1.O.[C:27]([O:30][CH2:31]C)(=[O:29])C>CN(C=O)C.CO>[CH:18]([C:17]1[C:16]([CH3:25])=[C:15]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([C:27]([O:30][CH3:31])=[O:29])[N:14]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH3:24])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 1177007533-(2-Chloropyrimidin-4-yl)-6-methoxy-2-methylbenzaldehyde

Product 1

HCID 117700769Methyl 4-(3-formyl-4-methoxy-2-methylphenyl)pyrimidine-2-carboxylateYield 33%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Triethylamine (656 μL, 4.71 mol) and a [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (256 mg, 0.314 mmol) were added to a solution of the 3-(2-chloropyrimidin-4-yl)-6-methoxy-2-methylbenzaldehyde obtained in Example 75-1 (412 mg, 1.57 mmol) in DMF (4.0 mL) and methanol (4.0 mL) at room temperature, and the mixture thus obtained was then stirred under a carbon monoxide atmosphere at 80° C. for 8 hours. Thereafter, the reaction solution was cooled to room temperature, and water was then added to the reaction solution. The mixed solution was extracted with ethyl acetate twice. The organic layer thus obtained was washed with water and brine, and was then dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 0:1, v/v) to obtain the title compound (150 mg, yield: 33%).

Workup

  1. customthe mixture thus obtained
  2. temperatureThereafter, the reaction solution was cooled to room temperature
  3. extractionThe mixed solution was extracted with ethyl acetate twice
  4. customThe organic layer thus obtained
  5. washwas washed with water and brine
  6. dry with materialwas then dried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled away under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-2c86814b3c0c4ff8b3674bf6047dd6ed
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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