4,6-Dichloropyrimidine → 1-(Tert-butoxycarbonyl)-4-[1-(6-chloro-pyrimidin-4-yl)-piperidin-4-ylcarbonyl]piperazine

HRID 2289561Notes

Reaction equation

HRID 2289561 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]([CH: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(=O)([O-])O.[Na+]>C(O)C>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][N:19]([C:22]([CH: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])[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 10803972Tert-butyl 4-(piperidine-4-carbonyl)piperazine-1-carboxylate

Product 1

HCID 186980351-(Tert-butoxycarbonyl)-4-[1-(6-chloro-pyrimidin-4-yl)-piperidin-4-ylcarbonyl]piperazineYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,6-dichloropyrimidine (3.60 g), 1-(tert-butoxycarbonyl)-4-(-4-piperidylcarbonyl)piperazine (6.00 g) and sodium hydrogen carbonate (4.20 g) in ethanol (100 ml) was heated at reflux for 6 hours. Solvent was evaporated and the residue dissolved in ethyl acetate and washed with water, dried (Na2SO4) and evaporated. The residue was recrystallised from ethyl acetate to give, as a solid 1-(tert-butoxycarbonyl)-4-[1-(6-chloro-pyrimidin-4-yl)-piperidin-4-ylcarbonyl]piperazine (7.40 g).

Workup

  1. temperatureat reflux for 6 hours
  2. customSolvent was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-0250639c463646639b0c0cacf2d16f18
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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