Water → 4-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]-benzaldehyde

HRID 257172Notes

Reaction equation

HRID 257172 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][N:11]([CH2:18][CH2:19][OH:20])[C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:10][N:11]([CH2:18][CH2:19][O:20][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:12]1[N:13]=[CH:14][CH:15]=[CH:16][N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 10419381Ethanol, 2-(methyl-2-pyrimidinylamino)-

Product 1

HCID 100380894-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-fluorobenzaldehyde (12 ml) and 2-[N-methyl-N-(2-pyrimidinyl)amino]ethanol (10.05 g) in dry dimethyl sulphoxide (50 ml) containing anhydrous potassium carbonate (15 g) was stirred at 120° C. for 6 hours. The mixture was cooled to room temperature and added to water (200 ml). The aqueous solution was extracted with ethyl acetate (2×300 ml), the organic extracts washed with brine, dried (MgSO4) and evaporated. The title compound was obtained as an oil following chromatography on silica-gel in 2% methanol in dichloromethane.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate (2×300 ml)
  3. washthe organic extracts washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-b9483360dc5c42278d322cddc8b3642d
Source dataset
uspto-grants-1993_11
Patent number
US05260445

Reaction notes

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