Phenol → HCID 59362908, compound

HRID 1668830Notes

Reaction equation

HRID 1668830 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]4[CH2:22][CH2:23][CH2:24][C:20]=4[N:19]=[C:18](Cl)[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[C:26]1([OH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.[Cu]>[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]4[CH2:22][CH2:23][CH2:24][C:20]=4[N:19]=[C:18]([O:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

7

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 59362943HCID 59362943, compound

Product 1

HCID 59362908HCID 59362908, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

The title compound was prepared following a published procedure in the literature (D'Angelo, N. D. et al. Tetrahedron Letters, 2006, 47, 5045-5048). A mixture of 1-[4-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]cyclobutane carboxylic acid methyl ester (0.45 g, 1.26 mmol), phenol (0.23 g, 2.5 mmol), copper powder (0.010 g) and cesium carbonate (1.25 g, 3.8 mmol) in anhydrous dimethylformamide (3 mL) was stirred at a temperature in the range of 10° C. to 100° C. for 6 to 20 hours. The mixture was cooled to about 20 to 35° C. and diluted with water. The organics were extracted with EtOAc and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by column chromatography (silica gel) to afford white solid (43% yield).

Workup

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

Sources & evidence

ORD record
ord-86382aee5bed4d0ca95cd6639d965f8e
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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