Phenol → HCID 12933872, compound

HRID 1668833Notes

Reaction equation

HRID 1668833 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=2[N:3]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cu]>[Cl:1][C:2]1[N:7]=[C:6]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]2[CH2:9][CH2:10][CH2:11][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidine

Product 1

HCID 12933872HCID 12933872, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.45 g, 2.4 mmol), phenol (0.28 g, 3 mmol), cesium carbonate (0.97 g, 3 mmol) and copper powder (0.01 g) in anhydrous dimethylformamide (5 mL) was stirred at about 20 to 35° C. for 6 to 20 hours. The reaction was quenched by addition of water. The organics were extracted with EtOAc and the combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude was purified by column chromatography (silica gel) to afford the title compound as a white solid (0.31 g, 54%).

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionThe organics were extracted with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-32ce6f3a6b4745e3a8830a08adbc265e
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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