Water → 4-[2-(2-Pyrimidinylamino)ethoxy]benzaldehyde

HRID 1292170Notes

Reaction equation

HRID 1292170 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[NH:9][CH2:10][CH2:11][OH:12].F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.O>CN(C=O)C>[N:3]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[NH:9][CH2:10][CH2:11][O:12][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 5727142-(Pyrimidin-2-ylamino)ethanol

Product 1

HCID 100146614-[2-(2-Pyrimidinylamino)ethoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (1.2 g; 60% dispersion in oil) was added portionwise to a stirred solution of 2-(2-pyrimidinyl amino)ethanol (4 g) in DMF (140 ml) under an atmosphere of nitrogen. After the vigorous reaction had subsided 4-fluorobenzaldehyde (5.35 g) was added and the solution heated to 80° C. for 20 hours. After cooling the mixture was added to water (500 ml) and extracted with diethyl ether (3×300 ml). The organic extracts were washed with brine (2×200 ml), dried (MgSO4), filtered and evaporated to dryness. Chromatography of the residue on silica gel in 2% methanol in dichloromethane afforded the title compound, which was used in the next stage without further purification.

Workup

  1. customAfter the vigorous reaction
  2. additionwas added
  3. temperatureAfter cooling the mixture
  4. extractionextracted with diethyl ether (3×300 ml)
  5. washThe organic extracts were washed with brine (2×200 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-a5b50eb2c8904f6a8e020bfa55026f15
Source dataset
uspto-grants-1998_05
Patent number
US05756525

Reaction notes

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