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Hydrochloric Acid → (+)-2-(4-(1-Propanoyloxyethyl)phenyl}-5-decyloxypyrimidine

HRID 274178
Notes
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Reaction equation

HRID 274178 reaction equation
N1C=CC=CC=1.[OH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH3:9].[C:33](Cl)(=[O:36])[CH2:34][CH3:35].Cl>O>[C:33]([O:7][CH:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:18][N:17]=2)=[CH:14][CH:15]=1)[CH3:9])(=[O:36])[CH2:34][CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 62324Propionyl chlorideHCID 214682802-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidine

Product 1

HCID 21468270(+)-2-(4-(1-Propanoyloxyethyl)phenyl}-5-decyloxypyrimidineYield 97%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Into 20 ml of pyridine were dissolved 1.78 g (5 millimole) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in the Preparation Example starting material compound (VI)] 70, and then 0.56 g (6 millimole) of propionic chloride was added thereto, to subject to reaction at 30 to 40° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into 200 ml of water, adjusted to pH 1 to 2 with 4N hydrochloric acid, and then extracted with 200 ml of toluene, followed by separation thereof. The organic phase was washed with water, 5% aqueous sodium hydrogen carbonate solution and water in this order. After drying over anhydrous magnesium sulfate, the residue obtained by distilling the organic solvent off under reduced pressure was purified by silica gel column chromatography (eluent; toluene: ethyl acetate) to obtain 2.00 g (yield: 97%) of (+)-2-(4-(1-Propanoyloxyethyl)phenyl}-5-decyloxypyrimidine.

Workup

  1. customto subject to reaction at 30 to 40° C. for 2 hours
  2. customAfter completion of the reaction
  3. extractionextracted with 200 ml of toluene
  4. customfollowed by separation
  5. washThe organic phase was washed with water, 5% aqueous sodium hydrogen carbonate solution and water in this order
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. customthe residue obtained
  8. distillationby distilling the organic solvent off under reduced pressure
  9. customwas purified by silica gel column chromatography (eluent; toluene: ethyl acetate)

Sources & evidence

ORD record
ord-b144768a10ff48e2938c7eaf39d68973
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05389293

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes