2,4,6-Trichloropyrimidine → HCID 19428493, compound

HRID 1078969Notes

Reaction equation

HRID 1078969 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[NH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13]>C(O)(C)C>[Cl:9][C:4]1[N:3]=[C:2]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=[C:6]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 773782,4,6-TrichloropyrimidineHCID 79882Neopentylamine

Product 1

HCID 19428493HCID 19428493, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

After dropwise adding 5.00 g (27.26 moles) of 2,4,6-trichloropyrimidine to the solution of 11.88 g (136.3 mmoles) of 1-amino-2,2-dimethylpropane in 50 ml of isopropanol while cooling and stirring, the reaction mixture is boiled under reflux for 20 hours, then evaporated. The evaporation residue is distributed between 80 ml of chloroform and 25 ml of 10% sodium hydroxide solution. After separation the organic phase is washed 4 times with 20 ml of water each, then dried and evaporated. The evaporation residue is subjected to chromatography by using a mixture of hexane and ethyl acetate as eluent on a silica gel column. By carrying out the elution with a 99:1 mixture, 6-chloro-2,4-bis(2,2-dimethylpropylamino)pyrimidine is obtained which is recrystallized from hexane to give a yield of 5.74 g (73.9%), m.p.: 95°-97° C.

Workup

  1. temperaturewhile cooling
  2. temperatureunder reflux for 20 hours
  3. customevaporated
  4. customAfter separation the organic phase
  5. washis washed 4 times with 20 ml of water each,
  6. customthen dried
  7. customevaporated
  8. additiona mixture of hexane and ethyl acetate as eluent on a silica gel column
  9. washthe elution with a 99:1 mixture

Sources & evidence

ORD record
ord-8dcf24199c484b7281e488a4c0fa5b30
Source dataset
uspto-grants-1996_08
Patent number
US05550240

Reaction notes

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