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

HRID 1692700Notes

Reaction equation

HRID 1692700 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-3-(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 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. 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
  10. filtrationover filter funnel

Sources & evidence

ORD record
ord-3b16dc57442446f694abdf61f50d9bc8
Source dataset
uspto-grants-2012_04
Patent number
US08158627B2

Reaction notes

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