Dicyclohexylcarbodiimide → HCID 19762061, compound

HRID 248777Notes

Reaction equation

HRID 248777 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][CH:15]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[F:25][C:26]([CH3:33])([CH2:30][CH2:31][CH3:32])[C:27](O)=[O:28].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:25][C:26]([CH3:33])([CH2:30][CH2:31][CH3:32])[C:27]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][CH:15]=3)=[N:12][CH:13]=2)=[CH:6][CH:7]=1)=[O:28]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 621975Phenol, 4-[2-(4-butoxyphenyl)-5-pyrimidinyl]-HCID 18924169140947-96-2

Product 1

HCID 19762061HCID 19762061, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3.6 g (0.01 mol) of 5-(4-hydroxyphenyl)-2-(4-butyloxyphenyl)pyrimidine, 1.5 g (0.01 mol) of (-)-2-fluoro-2-methylpentanoic acid, 2.1 g (0.01 mol) of N,N'-dicylohexylcarbodiimide (DCC) and 130 mg (1.0×10-3 mol) of 4-dimethylaminopyridine were dissolved in 190 ml of dried methylene chloride, which were stirred under reflux for 6 hours. After the completion of the reaction, the precipitate was removed by filtration and then the filtrate was washed with 1 normal hydrochloric acid and further with water and thereafter dried on anhydrous magnesium sulfate. After the removal of magnesium sulfate by filtration, the filtrate was purified through a column chromatography of silica gel with a developing solvent (toluene: ethyl acetate=10:1 (V/V)) and recrystallized from 30 ml of ethanol to obtain 660 mg (yield: 15%) of a white crystal. The thus obtained compound has the aforementioned physical and chemical properties.

Workup

  1. temperatureunder reflux for 6 hours
  2. customAfter the completion of the reaction
  3. customthe precipitate was removed by filtration
  4. washthe filtrate was washed with 1 normal hydrochloric acid and further with water
  5. dry with materialdried on anhydrous magnesium sulfate
  6. customAfter the removal of magnesium sulfate
  7. filtrationby filtration
  8. customthe filtrate was purified through a column chromatography of silica gel with a developing solvent (toluene: ethyl acetate=10:1 (V/V))
  9. customrecrystallized from 30 ml of ethanol

Sources & evidence

ORD record
ord-01fc8ba058a44009883e6279935d80d4
Source dataset
uspto-grants-1993_05
Patent number
US05211879

Reaction notes

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