2,4,6-Trichloropyrimidine → HCID 19428495, compound

HRID 1078955Notes

Reaction equation

HRID 1078955 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]([CH3:17])([CH3:16])[CH2:13][CH:14]=[CH2:15]>O1CCCC1>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:10][CH2:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH:14]=[CH2:15])[N:3]=1

Participants

4

Reactant 2

HCID 773782,4,6-TrichloropyrimidineHCID 6418312,2-dimethylpent-4-en-1-amine

Product 1

HCID 19428495HCID 19428495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.59 (25 mmoles) of 2,4,6-trichloropyrimidine are added to a solution of 6.23 g (55 mmoles) of 5-amino-4,4-dimethyl-1-pentene in 50 ml of tetrahydrofuran at room temperature, the reaction mixture is stirred at the same temperature for 4 hours, then evaporated. The evaporation residue is distributed between 60 ml of chloroform and 5 ml of 10% sodium hydroxide solution. After separation the organic phase is washed 4 times with 10 ml of water each, then dried and evaporated. The evaporation residue is subjected to chromatography on a silica gel column by using mixtures of hexane and ethyl acetate as eluents. Elution with a 19:1 hexane/ethyl acetate mixture gives 4,6-dichloro-2-[(2,2-dimethyl-4-penten-1-yl)amino]pyrimidine as an oily product in a yield of 2.62 g (40.3%).

Workup

  1. customevaporated
  2. customAfter separation the organic phase
  3. washis washed 4 times with 10 ml of water each,
  4. customthen dried
  5. customevaporated
  6. washElution with a 19:1 hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-c6d53bcacb0b486795e4a3ae6d1a2500
Source dataset
uspto-grants-1996_08
Patent number
US05550240

Reaction notes

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