Hexane → Tert-butyl 4-(5-ethylpyrimidin-2-yl)piperazine-1-carboxylate

HRID 271558Notes

Reaction equation

HRID 271558 reaction equation
[N:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:11]1[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=1.CCC[CH2:22][CH2:23][CH3:24].[CH3:25]COC(C)=O>CCO.C(N(CC)CC)C>[C:23]([O:8][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:11]2[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=2)[CH2:3][CH2:2]1)=[O:9])([CH3:22])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 131766Piperazine-1-carboxylic acidHCID 35727632-Chloro-5-ethylpyrimidine

Product 1

HCID 53305712Tert-butyl 4-(5-ethylpyrimidin-2-yl)piperazine-1-carboxylateYield 41%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

To piperazine-1-carboxylic acid .tert.-butyl ester (3.543 mmol) in EtOH (13 ml), triethylamine (1.5 ml) and 2-chloro-5-ethyl-pyrimidine (3.540 mmol) are added. The mixture is refluxed with stirring for 6 h. After cooling at room temperature, the reaction mixture is quenched with an ice water and extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and concentrated to give the product in 41% yield. Rf=0.45 (n-hexane:AcOEt=10:1) 1H NMR(400 MHz, CDCl3) δ 1.19 (t, 3H), 1.49 (s, 9H), 2.47 (q, 2H), 3.49 (dd, 4H), 3.76 (dd, 4H), 8.18 (s, 2H)

Workup

  1. temperatureThe mixture is refluxed
  2. customthe reaction mixture is quenched with an ice water
  3. extractionextracted with AcOEt
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give the product in 41% yield

Sources & evidence

ORD record
ord-89bb9428f6594941ac30e5acc50f4b5d
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

Loading…