Triethylamine → tert-Butyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylate

HRID 2289552Notes

Reaction equation

HRID 2289552 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>C(O)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 18697980tert-Butyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylateYield 87.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,6-dichloropyrimidine (10.05 g), tert-butoxycarbonylpiperazine (11.94 g) and triethylamine (28.20 ml) in ethanol (150 ml) was heated at reflux for 18 hours. Solvent was evaporated and the residue dissolved in ethyl acetate and washed with water, saturated aqueous ammonium chloride solution, dried (Na2SO4) and evaporated. Recrystallisation from ethyl acetate/hexane gave, as a solid 1-(tert-butoxycarbonyl)-4-(6-chloro-pyrimidin-4-yl)piperazine (16.80 g).

Workup

  1. temperatureat reflux for 18 hours
  2. customSolvent was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water, saturated aqueous ammonium chloride solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-414cbabc022149c8a414726351015ddb
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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