Piperazine → 6-Chloro-4-(piperazin-1-yl)pyrido[3,2-d]pyrimidine

HRID 1517403Notes

Reaction equation

HRID 1517403 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:9]2[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=2[N:11]=[CH:12][N:13]=1>O1CCOCC1>[N:1]1([C:8]2[C:9]3[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 105841654,6-Dichloropyrido[3,2-d]pyrimidine

Product 1

HCID 714076996-Chloro-4-(piperazin-1-yl)pyrido[3,2-d]pyrimidineYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of piperazine (7.0 g) in 1,4-dioxane (100 ml) was added a solution of crude 4,6-dichloro-pyrido[3,2-d]pyrimidine in 1,4-dioxane (50 ml). The resulting mixture was stirred at room temperature for 1 hour. After concentration under reduced pressure, the residue was purified by silica gel flash chromatography, the mobile phase being a methanol/dichloromethane mixture (in a ratio gradually ranging from 1:10 to 1:5), resulting in the pure title compound as a yellowish solid (3.1 g, yield 76%) which was characterized by its mass spectrum as follows: MS (m/z): 250.1 ([M+H]+, 100).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-ee0d8e4fedb64dc3a3651b0b050a4326
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

Loading…