Ethyl Acetate → HCID 9857771, compound

HRID 457876Notes

Reaction equation

HRID 457876 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:12][N:11]=[C:10]([NH2:20])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+].[C:26](OCC)(=[O:28])[CH3:27]>S(=O)(=O)(O)O.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:12][N:11]=[C:10]([NH:20][C:26](=[O:28])[CH3:27])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 9943253HCID 9943253, compound

Product 1

HCID 9857771HCID 9857771, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(3-fluorophenyl)-5-(4-pyridyl)-2-pyrimidinylamine (200 mg, 0.751 mmol) acetic anhydride (6 mL) and conc. sulfuric acid (4 drops) was stirred at 90° C. for 16 hours. After cooling as it was, the reaction solution was diluted with ethyl acetate, water and a saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated sodium bicarbonate (×2) and brine, and then dried over anhydrous sodium sulfate and concentrated. The residue was suspended in diethyl ether, and then the resulting solid was collected by filtration and washed with diethyl ether, to give the title compound (126 mg, 54%)

Workup

  1. temperatureAfter cooling as it
  2. washThe organic layer was washed with saturated sodium bicarbonate (×2) and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6e010f9850f64a4aa6cebcfb107c561b
Source dataset
uspto-grants-2007_03
Patent number
US07189717B2

Reaction notes

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