Triethylamine → 1-[1-(Tert-butoxycarbonyl)-piperazin-4-ylcarbonyl]-4-(6-chloro-pyrimidin-4-yl) piperazine

HRID 2289558Notes

Reaction equation

HRID 2289558 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][N:19]([C:22]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])[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:22]([N:24]2[CH2:29][CH2:28][N:27]([C:2]3[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=3)[CH2:26][CH2:25]2)=[O:23])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 18432746Tert-butyl 4-(piperazine-1-carbonyl)piperazine-1-carboxylate

Product 1

HCID 540504511-[1-(Tert-butoxycarbonyl)-piperazin-4-ylcarbonyl]-4-(6-chloro-pyrimidin-4-yl) piperazineYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,6-dichloropyrimidine (8.60 g), 1-[1-(tert-butoxycarbonyl)-piperazin-4-ylcarbonyl]piperazine 15.64 g) and triethylamine (21.95 ml) in ethanol (300 ml) was stirred at room temperature for 30 minutes. Solvent was evaporated and the residue dissolved in dichloromethane and washed with water, saturated aqueous sodium chloride solution, dried (Na2SO4) and evaporated to give, as a pale yellow solid 1-[1-(tert-butoxycarbonyl)-piperazin-4-ylcarbonyl]-4-(6-chloro-pyrimidin-4-yl) piperazine (21.20 g).

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water, saturated aqueous sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1a963b47e42446a4af3b6aacb81b30dd
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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