tert-Butyl piperazine-1-carboxylate → HCID 23070567, compound

HRID 501365Notes

Reaction equation

HRID 501365 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[N:9][C:10]([Cl:15])=[N:11][C:12]=2[Cl:14])[N:7]=[C:6]1Cl)[C:2]#[C:3][CH3:4].C(=O)(O)[O-].[Na+].[N:22]1([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(#N)C>[CH2:1]([N:5]1[C:13]2[C:8](=[N:9][C:10]([Cl:15])=[N:11][C:12]=2[Cl:14])[N:7]=[C:6]1[N:25]1[CH2:24][CH2:23][N:22]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27][CH2:26]1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylate2×HCID 516892Sodium Bicarbonate2×HCID 23070643HCID 23070643, compound

Product 1

HCID 23070567HCID 23070567, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.4 g of 7-(2-butynyl)-2,6,8-trichloro-7H-purine, 1.46 g of sodium bicarbonate, 2.43 g of t-butyl piperazine-1-carboxylate, and 45 ml of acetonitrile was stirred at room temperature for 2 hours and 20 minutes. Then, 0.73 g of sodium bicarbonate and 1.21 g of t-butyl piperazine-1-carboxylate were added, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with 1N hydrochloric acid, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was triturated with diethyl ether. The crystals were collected by filtration, and washed with diethyl ether. Thus, 3.0 g of the title compound was obtained as a white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. extractionThe reaction mixture was extracted with ethyl acetate-water
  3. washthe organic layer was washed with 1N hydrochloric acid
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with diethyl ether
  7. filtrationThe crystals were collected by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-2f0dca53a31547d9929cbda87e699820
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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