Allyl Alcohol → HCID 14717228, compound

HRID 1085884Notes

Reaction equation

HRID 1085884 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8](F)[CH:7]=[C:6]([F:11])[N:5]=1.[CH2:12]([OH:15])[CH:13]=[CH2:14]>>[CH2:12]([O:15][C:8]1[N:9]=[C:4]([NH2:3])[N:5]=[C:6]([F:11])[CH:7]=1)[CH:13]=[CH2:14]

Participants

4

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 12014802-Amino-4,6-difluoropyrimidine

Product 1

HCID 14717228HCID 14717228, compound

Conditions

Temperature
40 °C

Procedure

1.14 g (0.0382 mol) of 80% sodium hydride (emulsion in linseed oil) were added at 25° C. under a nitrogen atmosphere to 70 ml of allyl alcohol. To the clear solution obtained after stirring at 40° C. for 20 minutes were added 5.0 g (0.0382 mol) of 2-amino-4,6-difluoropyrimidine, and the mixture was then stirred at 97° C. for 1.5 hours. To work up, the excess alcohol was removed by distillation under reduced pressure, the residue was taken up in methylene chloride, and the solution was washed with water, dried over magnesium sulfate and then freed of solvent. The viscous oil obtained in this way crystallized on trituration with n-pentane. 4.6 g (71.2% of theory) of the title compound of melting point 62°-66° C. were obtained after filtering off, washing with water and drying.

Workup

  1. customTo the clear solution obtained
  2. stirringthe mixture was then stirred at 97° C. for 1.5 hours
  3. customthe excess alcohol was removed by distillation under reduced pressure
  4. washthe solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe viscous oil obtained in this way
  7. customcrystallized on trituration with n-pentane

Sources & evidence

ORD record
ord-cdb743a18ba54b09a13a36eff7018a6c
Source dataset
uspto-grants-1991_04
Patent number
US05011927

Reaction notes

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