Chloroacetonitrile → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[5-cyanomethylaminopentyl]pyrimidine

HRID 1462346Notes

Reaction equation

HRID 1462346 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][N:4]=[C:5]([NH2:19])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[N:8]=1.Cl[CH2:23][C:24]#[N:25].C(N(CC)CC)C>CCO>[F:21][C:2]([F:1])([F:20])[CH2:3][N:4]=[C:5]([NH2:19])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:23][C:24]#[N:25])[N:8]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 202086774-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidine

Product 1

HCID 202469524-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[5-cyanomethylaminopentyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidine (0.61 g.), chloroacetonitrile (0.17 g.) and triethylamine (0.23 g.) in EtOH (15 ml.) was heated under reflux for 7 hours. The solvent was evaporated and the residue was treated with sodium bicarbonate solution and extracted with EtOAc. The extract was dried (MgSO4) and evaporated to give an oil which was purified by medium pressure chromatography, eluting with 7.5% v/v MeOH in methylene chloride to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[5-cyanomethylaminopentyl]pyrimidine as a pale yellow solid which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. customThe solvent was evaporated
  4. additionthe residue was treated with sodium bicarbonate solution
  5. extractionextracted with EtOAc
  6. dry with materialThe extract was dried (MgSO4)
  7. customevaporated
  8. customto give an oil which
  9. customwas purified by medium pressure chromatography
  10. washeluting with 7.5% v/v MeOH in methylene chloride

Sources & evidence

ORD record
ord-3346560e8d47419bb730002ae812ffd8
Source dataset
uspto-grants-1984_07
Patent number
US04460584

Reaction notes

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