1-(2-Pyrimidinyl)piperazine → 4,6-Diphenyl-3-[4-(pyrimidin-2-yl)piperazin-1-yl]pyridazine

HRID 1479205Notes

Reaction equation

HRID 1479205 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[N:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[C:8]1([C:7]2[CH:6]=[C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:4]=[N:3][C:2]=2[N:29]2[CH2:30][CH2:31][N:26]([C:21]3[N:20]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:27][CH2:28]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 887471-(2-Pyrimidinyl)piperazineHCID 2781610HCID 2781610, compound

Product 1

HCID 236282464,6-Diphenyl-3-[4-(pyrimidin-2-yl)piperazin-1-yl]pyridazineYield 81.1%

Conditions

Temperature
130 °C

Procedure

A mixture of 3-chloro-4,6-diphenylpyridazine (267 mg, 1.0 mmol), 1-(2-pyrimidyl)piperazine (656 mg, 4.0 mmol) in 3 ml of 1-BuOH was heated with stirring at 130° C. for 3 days. 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 light pink solid. (320 mg, 0.81 mmol, yield 81.1%). ESI-MS: m/z 395.5 (M+H+). HRMS calcd 395.1979. Found 395.1973; 1H NMR (CDCl3): d 8.329 (d, J=5.0, 2H), 8.101 (d, J=7.5, 2H), 7.734 (d, J=7.5, 2H), 7.655 (s, 1H), 7.509 (m, 6H), 6.530 (t, 1H), 3.836 (t, J=4.5, J=5.0, 4H), 3.394 (t, J=5.0, J=4.5, 4H).

Workup

  1. temperaturewas heated
  2. customThe solvent was removed by evaporation in vacuo the residue
  3. additionwas 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
  9. customto give light pink solid

Sources & evidence

ORD record
ord-8004f33aaa9a4dda9cf93dadbaeab831
Source dataset
uspto-grants-2016_08
Patent number
US09408845B2

Reaction notes

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