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

HRID 383554Notes

Reaction equation

HRID 383554 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]pyridazine

Procedure

6-phenyl-3-(4-pyrimidin-2-ylpiperazin-1-yl)pyridazin-4-ol 1 h (22.0 g, 66 mmol) was suspended in 75 ml phosphorus oxychloride and heated with stirring at 100 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 filter 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 8.377 (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=4.0, J=4.5, 4H), 3.672 (t, J=4.0, J=4.5, 4H).

Workup

  1. temperatureheated
  2. additionwas poured
  3. customonto crushed ice
  4. customto give white suspension
  5. customThe precipitation
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried
  9. filtrationover filter funnel
  10. customto provide white solid

Sources & evidence

ORD record
ord-22f849f5cdd34c21b78c447cbf46c13b
Source dataset
uspto-grants-2013_02
Patent number
US08367672B2

Reaction notes

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