Sodium Hydroxide → 4-Chloro-6-phenyl-3-[4-(pyrimidin-2-yl)piperazin-1-yl]pyridazine

HRID 1479204Notes

Reaction equation

HRID 1479204 reaction equation
[C:1]1([C:7]2[N:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[N:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[CH2:15][CH2:14]3)=[C:9](O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:12]=[N:11][C:10]=1[N:13]1[CH2:18][CH2:17][N:16]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178515564HCID 178515564, compound

Product 1

HCID 444304154-Chloro-6-phenyl-3-[4-(pyrimidin-2-yl)piperazin-1-yl]pyridazineYield 91.4%

Conditions

Temperature
100 °C

Procedure

6-phenyl-(4-pyrimidin-2-ylpiperazin-1-yl)pyridazin-4-ol (22.0 g, 66 mmol) was suspended in 75 ml phosphorus oxychloride and heated with stirring at 100° C. for 3 h. After cooling to room temperature the mixture was poured onto crushed ice. The mixture was then neutralized with NaOH solution to give white suspension. The precipitation was filtered off, washed with water, dried over fitter funnel to provide white solid (21.3 g, 60.3 mmol, 91.4%). ESI-MS: m/z 353.4 (M+H+). 1H NMR (CDCl3): d 8377 (d, J=4.5, 2H), 8.036 (d, J=7.5, 2H), 7.833 (s, 1H), 7.508 (m, 3H), 6.564 (t, J=4.5, 1H), 4.073 (t, J=4.5, 4H), 3.672 (t, J=4.5, 4H).

Workup

  1. temperatureheated
  2. temperatureAfter cooling to room temperature the mixture
  3. additionwas poured
  4. customonto crushed ice
  5. customto give white suspension
  6. customThe precipitation
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried over fitter funnel

Sources & evidence

ORD record
ord-52cdc029e1ab4801a9afbe28d56cabe7
Source dataset
uspto-grants-2016_08
Patent number
US09408845B2

Reaction notes

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