Dimethylamine → HCID 19980405, compound

HRID 1461345Notes

Reaction equation

HRID 1461345 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]1([NH:10][C:11]2[N:16]=[C:15](Cl)[CH:14]=[C:13]([CH:18]3[CH2:20][CH2:19]3)[N:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[C:4]1([NH:10][C:11]2[N:16]=[C:15]([N:2]([CH3:3])[CH3:1])[CH:14]=[C:13]([CH:18]3[CH2:20][CH2:19]3)[N:12]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 19980404HCID 19980404, compound

Product 1

HCID 19980405HCID 19980405, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

17.9 ml of 33% (100 mmol) absolute ethanolic dimethylamine solution are added dropwise to 9.8 g (40 mmol) of 2-phenylamino-4-chloro-6-cyclopropyl-pyrimidine in 20 ml of absolute ethanol at room temperature in the course of 10 minutes, while stirring, and the yellow suspension formed is heated at 50° C. for one hour and then refluxed for a further hour. After evaporation of the solvent, the residue is taken up in 200 ml of methylene chloride and the mixture is washed twice with 100 ml of water each time, dried over sodium sulfate, filtered and freed from the methylene chloride by evaporation. The 10.2 g of a yellow oil which remain are purified by column chromatography over silica gel using methylene chloride as the mobile phase. After evaporation of the methylene chloride, a pale yellow oil remains, which crystallizes after some hours. The pale yellow crystals melt at 90°-91° C. Yield: 8.9 g (35 mmol; 87.5% of theory).

Workup

  1. customthe yellow suspension formed
  2. temperaturerefluxed for a further hour
  3. customAfter evaporation of the solvent
  4. washthe mixture is washed twice with 100 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customfreed from the methylene chloride by evaporation
  8. customThe 10.2 g of a yellow oil which remain are purified by column chromatography over silica gel
  9. customAfter evaporation of the methylene chloride
  10. customa pale yellow oil remains, which crystallizes after some hours
  11. custommelt at 90°-91° C

Sources & evidence

ORD record
ord-e4399f694fef4b06a28d332bc1028196
Source dataset
uspto-grants-1991_12
Patent number
US05075316

Reaction notes

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