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

HRID 544569Notes

Reaction equation

HRID 544569 reaction equation
Cl.[Cl:2][CH2:3][C:4]([NH2:6])=[NH:5].C(N(CC)CC)C.Cl[C:15](=[CH2:18])[C:16]#[N:17]>CCO>[NH2:17][C:16]1[CH:15]=[CH:18][N:6]=[C:4]([CH2:3][Cl:2])[N:5]=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

To a solution of chloroacetamidine hydrochloride (11 g.) in EtOH (50 ml.) was added triethylamine (24 ml.) and 2-chloroacrylonitrile (6.8 ml.) and the mixture was heated under reflux for 10 minutes. The dark solution was evaporated to dryness in vacuo, the residue dissolved in EtOAc, the solution decolourised with carbon, filtered and the filtrate evaporated. Ether was added and the solution filtered to remove some insoluble material. Evaporation gave 4-amino-2-chloromethylpyrimidine (5 g.), m.p. 125°-128°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 minutes
  3. customThe dark solution was evaporated to dryness in vacuo
  4. dissolutionthe residue dissolved in EtOAc
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. additionEther was added
  8. filtrationthe solution filtered
  9. customto remove some insoluble material
  10. customEvaporation

Sources & evidence

ORD record
ord-01c5e0f2479a41a7b87a0665746b90ec
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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