4-Fluorophenol → HCID 118022623, compound

HRID 1498860Notes

Reaction equation

HRID 1498860 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>N1C=CC=CC=1.C(OCC)(=O)C.[Cu]>[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:2]2[CH:3]=[N:4][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 21914476tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate

Product 1

HCID 118022623HCID 118022623, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (684 mg, 2.0 mmol), 4-fluorophenol (1.1 g, 5.0 mmol), copper (650 mg, 10.0 mmol) and Cs2CO3 (6.5 g, 20.0 mmol) in pyridine (15 mL) was heated at 120° C. for 12 h. The mixture was cooled to RT, diluted with ethyl acetate (200 mL) and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=20/1) to afford the title compound (200 mg, 27%) as a brown solid. MS (ES+) C19H23FN4O3 requires: 374. found: 319 [M−56+1]+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-aea0c35bcdfd48139de8c45c70bfff0b
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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