Ethanol → HCID 13910043, compound

HRID 231112Notes

Reaction equation

HRID 231112 reaction equation
[Cl:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19]CO)=[CH:15][C:14]=2[CH3:22])=[N:4][CH:5]=[N:6][C:7]=1[CH3:8].[H-].[Na+].[CH2:25]([O:27][CH2:28][CH2:29]Br)[CH3:26].C([OH:33])C>O1CCCC1.O>[Cl:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][O:33][CH2:29][CH2:28][O:27][CH2:25][CH3:26])=[CH:15][C:14]=2[CH3:22])=[N:4][CH:5]=[N:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 702EthanolHCID 24758Sodium hydride2×HCID 611412-Bromoethyl ethyl etherHCID 15052848HCID 15052848, compound

Product 1

HCID 13910043HCID 13910043, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.1 g of 5-chloro-4-{2-[4-(2-hydroxyethyl)-2-methylphenoxy]ethylamino}-6-methylpyrimidine were dissolved in 50 ml of anhydrous tetrahydrofuran and 0.3 g of sodium hydride (which had been freed from mineral oil by washing with hexane) were added to the solution. The mixture was stirred at room temperature for 30 minutes. 1.7 g of 2-bromoethyl ethyl ether was added to the mixture and it was then stirred, whilst heating, for 3 hours. At the end of this time, any excess of sodium hydride was decomposed by adding ethanol. Water was added to the mixture, and the oily substance which separated was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. Ethyl acetate was removed by distillation under reduced pressure to give an oily substance which was subjected to column chromatography (Wakogel C-200, eluted with a 2:1 by volume mixture of toluene and ethyl acetate) to afford 2.0 g of the title compound as a pale yellow oily liquid, n16.4 = 1.5591.

Workup

  1. stirringwas then stirred
  2. temperaturewhilst heating, for 3 hours
  3. customthe oily substance which separated
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEthyl acetate was removed by distillation under reduced pressure
  8. customto give an oily substance which
  9. washeluted with a 2:1 by volume mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-24fcfc53ba0a4b708d1e1a24748af5aa
Source dataset
uspto-grants-1989_07
Patent number
US04845097

Reaction notes

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