Potassium Carbonate → HCID 54111344, compound

HRID 1941061Notes

Reaction equation

HRID 1941061 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:15]1[CH:16]=[N:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[N:19][CH:20]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl[CH2:29][CH:30]([OH:43])[CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][CH2:41][CH3:42]>CN(C)C=O.O>[CH2:7]([C:15]1[CH:20]=[N:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:29][C@@H:30]([OH:43])[CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:23][CH:22]=2)=[N:17][CH:16]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 34731571-[2-(2-butoxyethoxy)ethoxy]-3-chloropropan-2-ol

Product 1

HCID 54111344HCID 54111344, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.1 g, 15.7 mmol) was added to a solution of 5-octyl-2-(4-hydroxyphenyl)pyrimidine (3.0 g, 10.5 mmol) and 1-chloro-3-(2-(2-butoxyethoxy)ethoxy)-2-propanol (2.7 g, 10.5 mmol) in N,N-dimethylformamide (100 ml). The resulting mixture was stirred at reflux temperature for 18 hours and then cooled to ambient temperature. The mixture was diluted with water (100 ml) and was extracted with three 100 ml aliquots of diethyl ether. The extracts were dried (over MgSO4), filtered, and concentrated to give crude product as an oil. 5-Octyl-2-[4-((S)-2-hydroxy-3-(2-(2-(butoxy)ethoxy)ethoxy)propoxy)phenyl]pyrimidine was then isolated by chromatography. The chiral (S)-hydroxy compound (3.5 g, 7.5 mmol) was treated with diethylaminosulfur trifluoride (5.3 g, 15 mmol) to produce Comparative Example 1.

Workup

  1. temperatureat reflux temperature for 18 hours
  2. extractionwas extracted with three 100 ml aliquots of diethyl ether
  3. dry with materialThe extracts were dried (over MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product as an oil

Sources & evidence

ORD record
ord-7abee4137e2a4122b22fd2eeb752173d
Source dataset
uspto-grants-1997_12
Patent number
US05702637

Reaction notes

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