3-Chloro-4-fluoroaniline → HCID 21830556, compound

HRID 725851Notes

Reaction equation

HRID 725851 reaction equation
O[C:2]1[C:3]2[N:11]=[C:10]([S:12][CH3:13])[N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C[Si](C)(C)N[Si](C)(C)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[F:31])[NH2:27].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:23][C:24]1[CH:25]=[C:26]([NH:27][C:2]2[C:3]3[N:11]=[C:10]([S:12][CH3:13])[N:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:28]=[CH:29][C:30]=1[F:31]

Participants

6

Reactant 4

HCID 97083-Chloro-4-fluoroanilineHCID 13838HexamethyldisilazaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 1785034026-methylsulfanyl-1H-pyrimido[5,4-d]pyrimidin-4-one

Product 1

HCID 21830556HCID 21830556, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound may be obtained in the following way: a mixture of 10 g 4-hydroxy-6-methylthio-pyrimido[5,4-d]pyrimidine, 16 ml hexamethyldisilazane, 32.5 g 3-chloro-4-fluoro-aniline and 1 g p-toluenesulphonic acid hydrate are heated at boiling point for 12 hours. Then 500 ml methanol is added and the mixture heated at boiling point for a further hour. The solvents are distilled off in a rotary evaporator, the residue is dissolved in methylene chloride, the solution is extracted with 100 ml 2N sodium hydroxide and dried over magnesium sulfate. After distilling off the solvent in a rotary evaporator the residue is triturated with 200 ml ether, filtered off and washed several times with ether.

Workup

  1. customThis compound may be obtained in the following way
  2. temperatureare heated
  3. customfor 12 hours
  4. temperaturethe mixture heated
  5. distillationThe solvents are distilled off in a rotary evaporator
  6. dissolutionthe residue is dissolved in methylene chloride
  7. extractionthe solution is extracted with 100 ml 2N sodium hydroxide
  8. dry with materialdried over magnesium sulfate
  9. distillationAfter distilling off the solvent
  10. customin a rotary evaporator the residue
  11. customis triturated with 200 ml ether
  12. filtrationfiltered off
  13. washwashed several times with ether

Sources & evidence

ORD record
ord-0f0d98c8f5ff4ed59ac7da6d72b62d99
Source dataset
uspto-grants-1998_01
Patent number
US05707989

Reaction notes

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