4-Fluorophenol → HCID 57782285, compound

HRID 1670851Notes

Reaction equation

HRID 1670851 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O-:12])([O-])=O.[Cs+].[Cs+].[CH3:15][N:16]1[C:21](=O)[N:20]([CH3:23])[CH2:19][CH2:18]C1>CCOC(C)=O.CCCCCC>[CH2:19]([N:20]1[C:23]([CH:9]=[O:12])=[CH:15][N:16]=[C:21]1[O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:18]

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-

Product 1

HCID 57782285HCID 57782285, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
200 °C

Procedure

A suspension of the compound obtained in Example 7-(1) (5.0 g), 4-fluorophenol (2.87 g) and Cs2CO3 (10.4 g) in DMPU (10 ml) was stirred at 200° C. for 1 hour. After cooling to room temperature, the reaction mixture was diluted with methanol/chloroform (1/4) and filtered. The filtrate was concentrated, and the resulting residue was purified by column chromatography (OH-type SiO2, AcOEt/hexane=0% to 30%) to give the titled compound (4.16 g) as a light-pink liquid.

Workup

  1. additionA suspension of the compound
  2. temperatureAfter cooling to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe resulting residue was purified by column chromatography (OH-type SiO2, AcOEt/hexane=0% to 30%)

Sources & evidence

ORD record
ord-82e7df02b0c449319b2557fb0eb3c72c
Source dataset
uspto-grants-2011_08
Patent number
US07994204B2

Reaction notes

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