Triethylamine → 2-(Chloromethyl)pyrimidin-4-amine

HRID 543773Notes

Reaction equation

HRID 543773 reaction equation
Cl[C:2](=[CH2:5])[C:3]#[N:4].Cl.[Cl:7][CH2:8][C:9]([NH2:11])=[NH:10].C(N(CC)CC)C>CCO>[NH2:4][C:3]1[CH:2]=[CH:5][N:11]=[C:9]([CH2:8][Cl:7])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 27769572-Chloroacetamidine monohydrochloride

Product 1

HCID 212988272-(Chloromethyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloroacrylonitrile (35 ml.) was added in portions over 15 minutes to a solution of chloroacetamidine hydrochloride (55 g.) and triethylamine (120 ml.) in EtOH (250 ml.) cooled to 10°. The temperature was allowed to rise to 40° over 1 hour. The mixture was cooled and filtered and the resulting solution evaporated in vacuo. The residue was taken up in EtOAc (600 ml.) from which a tar precipitated. The solution was treated with decolourising carbon, filtered and evaporated to give 4-amino-2-chloromethylpyrimidine as a brown solid.

Workup

  1. temperaturecooled to 10°
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe resulting solution evaporated in vacuo
  5. customprecipitated
  6. additionThe solution was treated with decolourising carbon
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4605f06af2ed4a0abcb4827ca40e2889
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

Loading…