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

HRID 1721297Notes

Reaction equation

HRID 1721297 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

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

Workup

  1. temperaturecooling
  2. stirringThereafter, the reaction mixture is stirred at room temperature for an additional 30 minutes
  3. customevaporated
  4. customthe organic phase is separated
  5. washwashed 4 times with 100 ml of water each,
  6. customthen dried
  7. customevaporated
  8. additiona 19:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-f44c43a42904454388914e3ab44a822f
Source dataset
uspto-grants-1996_04
Patent number
US05510345

Reaction notes

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