Ammonia → HCID 17848708, compound

HRID 457877Notes

Reaction equation

HRID 457877 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]=[C:16](F)[CH:15]=3)=[CH:12][N:11]=[C:10]([NH2:21])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH3:22].C(O)C.N>C(O)C>[NH2:22][C:16]1[CH:15]=[C:14]([C:13]2[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][C:10]([NH2:21])=[N:11][CH:12]=2)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 17848732HCID 17848732, compoundHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 17848708HCID 17848708, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(3-fluorophenyl)-5-(2-fluoro-4-pyridyl)-2-pyrimidinylamine (100 mg, 0.352 mmol) and ammonia/ethanol (ethanol saturated with an ammonia gas under ice-cooling) (20 mL) was sealed in a test tube and stirred at 150° C. for 2 weeks. After cooling as it was, the reaction solution was concentrated. The residue was dissolved by adding ethyl acetate and water thereto. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate and concentrated. The residue was purified by TLC plate (eluting solvent: dichloromethane/methanol=10/1), to give the title compound (12 mg, 12%).

Workup

  1. temperaturecooling) (20 mL)
  2. customwas sealed in a test tube
  3. temperatureAfter cooling as it
  4. concentrationthe reaction solution was concentrated
  5. dissolutionThe residue was dissolved
  6. additionby adding ethyl acetate and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by TLC plate (eluting solvent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-e80391f8c20649d2983756ad1c0c2f0b
Source dataset
uspto-grants-2007_03
Patent number
US07189717B2

Reaction notes

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