Methanol → HCID 23020468, compound

HRID 747153Notes

Reaction equation

HRID 747153 reaction equation
[Na].Cl[C:3]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:6]=[C:5]([NH2:22])[N:4]=1.[CH3:23][OH:24]>C(OCC)(=O)C>[F:21][C:17]1[CH:16]=[C:15]([C:7]2[C:8]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)=[C:3]([O:24][CH3:23])[N:4]=[C:5]([NH2:22])[N:6]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 23020409HCID 23020409, compound

Product 1

HCID 23020468HCID 23020468, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
62.5 °C

Procedure

After sodium (20 mg, 0.870 mmol) was dissolved in methanol (3 ml), 4-chloro-6-(3-fluorophenyl)-5-(4-pyridyl)-2-pyrimidinylamine (50 mg, 0.166 mmol) was added thereto and the mixture was stirred under an atmosphere of nitrogen gas at 60 to 65° C. for 30 minutes. After cooling as it was, the reaction mixture was diluted with ethyl acetate. Then, the mixture was washed with an aqueous ammonium chloride solution thrice and brine, dried over anhydrous sodium sulfate and concentrated. To the residue was added diethyl ether, and the resulting precipitates were collected by filtration and washed with diethyl ether, to give the title compound (16 mg, 32%) as a colorless solid.

Workup

  1. temperatureAfter cooling as it
  2. washThen, the mixture was washed with an aqueous ammonium chloride solution thrice and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionTo the residue was added diethyl ether
  6. customthe resulting precipitates
  7. filtrationwere collected by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-e7e779785c0b488c85e9afe213626c59
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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