2,4,6-Trichloropyrimidine → HCID 19428516, compound

HRID 1078291Notes

Reaction equation

HRID 1078291 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[NH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13]>O1CCCC1>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[N:3]=1

Participants

4

Reactant 2

HCID 773782,4,6-TrichloropyrimidineHCID 79882Neopentylamine

Product 1

HCID 19428516HCID 19428516, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dropwise adding 25 g (136.3 mmoles) of 2,4,6-trichloropyrimidine to a solution of 23.84 g (273.5 mmoles) of 1-amino-2,2-dimethylpropane in 200 ml of tetrahydrofuran at a temperature between 10° and 15° C. while cooling under stirring, the reaction mixture is stirred at room temperature for 30 minutes, then evaporated. The residue is distributed between 300 ml of chloroform and 50 ml of 10% sodium hydroxide solution. After separation the organic phase is washed 4 times with 100 ml of water each, dried and evaporated. The residue is subjected to chromatography on a silica gel column by using mixtures of hexane/ethyl acetate elution. By eluting with a 19:1 mixture, 4,6-dichloro-2-(2,2-dimethylpropylamino) pyrimidine is obtained which is recrystallized from a mixture of ether and hexane to give a yield of 13.60 g (42.6%), m.p.:63°-66° C.

Workup

  1. temperaturewhile cooling
  2. stirringthe reaction mixture is stirred at room temperature for 30 minutes
  3. customevaporated
  4. customAfter separation the organic phase
  5. washis washed 4 times with 100 ml of water each,
  6. customdried
  7. customevaporated
  8. washmixtures of hexane/ethyl acetate elution
  9. washBy eluting with a 19:1 mixture

Sources & evidence

ORD record
ord-290ade7c9fb444eeb153a65392c7f8fa
Source dataset
uspto-grants-1996_08
Patent number
US05547949

Reaction notes

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