Phosphorus oxychloride → 4-Tert-butyl-6-chloropyrimidin-2-amine

HRID 343841Notes

Reaction equation

HRID 343841 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[N:3]=1.P(Cl)(Cl)([Cl:15])=O>>[NH2:1][C:2]1[N:7]=[C:6]([Cl:15])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178441204HCID 178441204, compound

Product 1

HCID 218463784-Tert-butyl-6-chloropyrimidin-2-amine

Procedure

2-Amino-4-hydroxy-6-tert-butylpyrimidine (8.35 g) was dissolved in 50 mL of phosphorus oxychloride and the solution refluxed for 2 hours. Excess phosphorus oxychloride was removed under vacuum and the residue dissolved in 100 mL of ethanol. The solution was adjusted to pH 8 with ice-cold concentrated ammonium hydroxide, and solvent removed under reduced pressure. The residue was filtered to give a white solid, which was recrystallized from ethanol-water to give 2-amino-4-chloro-6-tert-butylpyrimidine (3.66 g), m.p. 87.7°-88.9° C.

Workup

  1. temperaturethe solution refluxed for 2 hours
  2. customExcess phosphorus oxychloride was removed under vacuum
  3. dissolutionthe residue dissolved in 100 mL of ethanol
  4. customremoved under reduced pressure
  5. filtrationThe residue was filtered
  6. customto give a white solid, which
  7. customwas recrystallized from ethanol-water

Sources & evidence

ORD record
ord-658ade5684834f96abb7682ef720f0c2
Source dataset
uspto-grants-1999_01
Patent number
US05863924

Reaction notes

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