4-Fluoroaniline → 5-bromo-2-(4-fluorophenylamino)-3-methylpyrimidin-4(3H)-one

HRID 2241255Notes

Reaction equation

HRID 2241255 reaction equation
[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](Cl)=[N:6][CH:7]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>CCCCO.CCOC(C)=O>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 97314-FluoroanilineHCID 516892Sodium BicarbonateHCID 673486115-bromo-2-chloro-3-methylpyrimidin-4(3H)-one

Product 1

HCID 685151905-bromo-2-(4-fluorophenylamino)-3-methylpyrimidin-4(3H)-oneYield 99%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-2-chloro-3-methylpyrimidin-4(3H)-one (0.100 g, 0.448 mmol; prepared according to the procedure of Example 46, Step B), 4-fluorobenzenamine (0.056 ml, 0.582 mmol) and NaHCO3 (0.150 g, 1.79 mmol) in n-BuOH (3 mL) was stirred at 60° C. overnight. The reaction mixture was cooled to room temperature and then diluted with EtOAc. The EtOAc layer washed with H2O and saturated aqueous NaCl. The aqueous phase was re-extracted with EtOAc. The combined EtOAc layers were dried (Na2SO4), filtered and concentrated to yield the desired product (0.132 g, 99%) as a pale yellow solid that was used without further purification.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washThe EtOAc layer washed with H2O and saturated aqueous NaCl
  4. extractionThe aqueous phase was re-extracted with EtOAc
  5. dry with materialThe combined EtOAc layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-14202cdaf4284259b330f52746160049
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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