P-Cresol → HCID 57782331, compound

HRID 1670848Notes

Reaction equation

HRID 1670848 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:15][N:16]1[C:21](=O)[N:20]([CH3:23])[CH2:19][CH2:18]C1>O>[CH2:19]([N:20]1[CH:23]=[CH:15][N:16]=[C:21]1[O:7][C:6]1[CH:5]=[CH:4][C:3]([CH3:8])=[CH:2][CH:1]=1)[CH3:18]

Participants

5

Reactant 3

HCID 2879P-CresolHCID 10796Cesium carbonateHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-

Product 1

HCID 57782331HCID 57782331, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of the compound obtained in Example 1-(1) (30.27 g), 4-cresol (17.69 g), Cs2CO3 (53.43 g) and N,N′-dimethylpropyleneurea (DMPU) (136 ml) was stirred at 200° C. for 3 hours. The mixture was cooled to room temperature, diluted with water, and extracted with AcOEt. After washing with brine, the organic layer was dried over MgSO4, filtered and evaporated under reduced pressure to remove the solvent. The resulting crude product was purified by column chromatography (neutral OH-type SiO2, hexane/AcOEt=10% to 40%) to give the titled compound (8.54 g, yellow oil).

Workup

  1. additionA mixture of the compound
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with AcOEt
  4. washAfter washing with brine
  5. dry with materialthe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto remove the solvent
  9. customThe resulting crude product was purified by column chromatography (neutral OH-type SiO2, hexane/AcOEt=10% to 40%)

Sources & evidence

ORD record
ord-f0e1b8c5371c4801aedb3598c54f50eb
Source dataset
uspto-grants-2011_08
Patent number
US07994204B2

Reaction notes

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