1-(2-Pyrimidinyl)piperazine → 2-(4-(6-Chloro-5-phenylpyridazin-3-yl)piperazin-1-yl)pyrimidine

HRID 383557Notes

Reaction equation

HRID 383557 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:24]2[CH2:25][CH2:26][N:21]([C:16]3[N:15]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:22][CH2:23]2)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 887471-(2-Pyrimidinyl)piperazineHCID 113220803,6-Dichloro-4-phenylpyridazine

Product 1

HCID 862421262-(4-(6-Chloro-5-phenylpyridazin-3-yl)piperazin-1-yl)pyrimidineYield 86.7%

Conditions

Temperature
80 °C

Procedure

A mixture of 3,6-dichloro-4-phenylpyridazine (1.35 g, 6 mmol), 1-(2-pyrimidyl)piperazine (1.2 g, 6.0 mmol) in 10 ml of 1-BuOH was heated with stirring at 80° C. for 12 h. The solvent was removed by evaporation in vacuo, the residue was treated with water to give a suspension. The solid was then filtered off, washed with water, dried over filter funnel in vacuo to give white solid (1.8 g, 5.2 mmol, yield 86.0%). ESI-MS: m/z 353.9.

Workup

  1. temperaturewas heated
  2. customThe solvent was removed by evaporation in vacuo
  3. additionthe residue was treated with water
  4. customto give a suspension
  5. filtrationThe solid was then filtered off
  6. washwashed with water
  7. customdried
  8. filtrationover filter funnel in vacuo

Sources & evidence

ORD record
ord-fa303e0a7c77467e9801eefb7a537dad
Source dataset
uspto-grants-2013_02
Patent number
US08367672B2

Reaction notes

Loading…