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

HRID 896220Notes

Reaction equation

HRID 896220 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]([CH2:17][CH2:18][CH3:19])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][CH2:22][CH2:23][Cl:24].C(N(CC)CC)C>C(#N)C>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:21][CH2:22][CH2:23][Cl:24])[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH2:17][CH2:18][CH3:19])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 22349857HCID 22349857, compound

Product 1

HCID 223498642-Tert-butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-propyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15 g of 2-tert-butyl-4-piperazin-1-yl-6-propyl-pyrimidine (57.2 mmol), 9 g of 1-bromo-3-chloropropane (57.2 mmol), 8.7 g of triethylamine (86.2 mmol) in 200 ml of acetonitrile were heated to reflux for 3 h. The precipitate was filtered off and the remaining filtrate evaporated to dryness. The thus obtained crude product was purified by chromatography on silica gel with dichloromethane/methanol (0-5%). Yield: 6 g (31%).

Workup

  1. temperatureto reflux for 3 h
  2. filtrationThe precipitate was filtered off
  3. customthe remaining filtrate evaporated to dryness
  4. customThe thus obtained crude product
  5. customwas purified by chromatography on silica gel with dichloromethane/methanol (0-5%)

Sources & evidence

ORD record
ord-08c3b7ef64904298a4c30a4c0828ddc7
Source dataset
uspto-grants-2005_07
Patent number
US06919342B2

Reaction notes

Loading…