Sodium Methoxide → HCID 19980403, compound

HRID 1461344Notes

Reaction equation

HRID 1461344 reaction equation
[C:1]1([NH:7][C:8]2[N:13]=[C:12](Cl)[CH:11]=[C:10]([CH:15]3[CH2:17][CH2:16]3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O-:19].[Na+]>O1CCOCC1.CO>[C:1]1([NH:7][C:8]2[N:13]=[C:12]([O:19][CH3:18])[CH:11]=[C:10]([CH:15]3[CH2:17][CH2:16]3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 19980404HCID 19980404, compound

Product 1

HCID 19980403HCID 19980403, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

6.87 g (28 mmol) of 2-phenylamino-4-chloro-6-cyclopropyl-pyrimidine in 25 ml of dioxane are added dropwise to 5.8 g (32.2 mmol) of sodium methylate in 10 ml of absolute methanol at room temperature in the course of half an hour, while stirring, and the mixture is then heated at 50° C. for 6 hours. To bring the reaction to completion, a further 0.76 g (4.2 mmol) of sodium methylate is added and the mixture is heated at 50° C. for a further 20 hours. After evaporation of the solvent, 300 ml of diethyl ether are added to the residue, the suspension is washed twice with 100 ml of water each time and then dried over sodium sulfate and filtered and the diethyl ether is evaporated off. 6.7 g of yellow oil which remain are purified by column chromatography over silica gel using toluene as the mobile phase. After evaporation of the toluene, a pale yellow oil of refractive index nD25 : 1.6225 remains. Yield: 5.8 g (24 mmol; 86% of theory).

Workup

  1. customthe reaction to completion
  2. temperaturethe mixture is heated at 50° C. for a further 20 hours
  3. customAfter evaporation of the solvent, 300 ml of diethyl ether
  4. additionare added to the residue
  5. washthe suspension is washed twice with 100 ml of water each time
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe diethyl ether is evaporated off
  9. custom6.7 g of yellow oil which remain are purified by column chromatography over silica gel
  10. customAfter evaporation of the toluene

Sources & evidence

ORD record
ord-b4eda319b027463b8cd71b7e213eb734
Source dataset
uspto-grants-1991_12
Patent number
US05075316

Reaction notes

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