1-Bromo-3-chloropropane → 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-tert-butyl-pyrimidine

HRID 896219Notes

Reaction equation

HRID 896219 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][CH2:23][CH2:24][Cl:25].[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:22][CH2:23][CH2:24][Cl:25])[CH2:13][CH2:12]2)[CH:8]=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 114600842,4-Di-tert-butyl-6-piperazin-1-ylpyrimidine

Product 1

HCID 223498712-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-tert-butyl-pyrimidineYield 82%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

40 g of 2-tert-butyl-4-[piperazin-1-yl]-6-tert-butyl-pyrimidine and 45.6 g of 1-bromo-3-chloro-propane were dissolved in 160 ml toluene. 13.3 g of 50% aqueous sodium hydroxide and 2.3 g of tetrabutylammonium bromide (dissolved in 40 ml water) were added. The mixture was kept at 50° C. for 5 h under vigorous stirring. The reaction mixture was then extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The product was purified by chromatography on silicagel (cyclohexane/0-10% ethyl acetate) to yield the title compound in 82% yield.

Workup

  1. extractionThe reaction mixture was then extracted with water and ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe product was purified by chromatography on silicagel (cyclohexane/0-10% ethyl acetate)

Sources & evidence

ORD record
ord-829f4546959e4749ae1a18181d29e714
Source dataset
uspto-grants-2005_07
Patent number
US06919342B2

Reaction notes

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