4-Toluenesulfonyl chloride → (S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexylpyrimidine

HRID 274202Notes

Reaction equation

HRID 274202 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[Cl:12][C@@H:13]([CH3:17])[CH2:14][CH2:15][OH:16].[CH2:18]([C:24]1[CH:25]=[N:26][C:27]([C:30]2[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=2)=[N:28][CH:29]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:12][C@@H:13]([CH3:17])[CH2:14][CH2:15][O:16][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[N:26]=[CH:25][C:24]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:29][N:28]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 641048(S)-3-chlorobutan-1-olHCID 30922104-(5-Hexyl-2-pyrimidinyl)phenol

Product 1

HCID 67801633(S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexylpyrimidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

26.3 g of (S)-3-chlorobutyl-1-tosylate, preparable from p-toluenesulfonyl chloride and (S)-3-chlorobutan-1-ol, and 27.2 g of 4-(5-n-hexylpyrimidin-2-yl)phenol are added to a suspension of 40 g of potassium carbonate in 200 ml of acetone. After 24 hours, boiling under reflux, the reaction mixture is filtered, the filtrate is freed from solvent and the residue is twice recrystallized from ethanol. (S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexyl-pyrimidine is obtained.

Workup

  1. temperatureunder reflux
  2. filtrationthe reaction mixture is filtered
  3. customthe residue is twice recrystallized from ethanol

Sources & evidence

ORD record
ord-40c7d00b92814a4fa5129238434cb585
Source dataset
uspto-grants-1995_02
Patent number
US05389290

Reaction notes

Loading…