1-(2-Pyrimidinyl)piperazine → HCID 17755564, compound

HRID 1425726Notes

Reaction equation

HRID 1425726 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:14])=[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>>[CH3:14][C:5]1[N:4]=[N:3][C:2]([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)=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1

Participants

3

Reactant 2

HCID 887471-(2-Pyrimidinyl)piperazineHCID 64152403-chloro-6-methyl-4-phenylpyridazine

Product 1

HCID 17755564HCID 17755564, compoundYield 41.7%

Procedure

A synthetic reaction scheme for the preparation of6-methyl-4-phenyl-3-(4-pyrimidin-2-ylpiperazin-1-yl)pyridazine (MW01-7-057) is depicted in FIG. 26, and synthesis was carried out as described herein. A mixture of 3-chloro-6-methyl-4-phenylpyridazine (100 mg, 0.5 mmol), 1-(2-pyrimidyl)piperazine (400 mg, 2.0 mmol) in 3 ml of 1-BuOH was heated with stirring at 130 C for 7 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, then 1:3, Ethyl Acetate: Petroleum ether, dried over filter funnel in vacuo to give, light yellow solid (68 mg, 0.20 mmol, yield 41.7%). Purity>95%; ESI-MS: m/z 333.1 (M+H+). 1H NMR (CDCl3): d 8.310 (d, J=5.0, 2H), 7.678 (d, J=7.5, 2H), 7.476 (m, 3H), 7.119 (s, H), 6.509 (t, J=4.5, 1H), 3.785 (t, J=4.5, J=5.0, 4H), 3.277 J=4.5, J=5.0, 4H), 2.669 (s, 3H).

Workup

  1. customA synthetic reaction scheme
  2. customis depicted in FIG. 26, and synthesis
  3. temperaturewas heated
  4. customThe solvent was removed by evaporation in vacuo
  5. additionthe residue was treated with water
  6. customto give a suspension
  7. filtrationThe solid was then filtered off
  8. washwashed with water
  9. dry with material1:3, Ethyl Acetate: Petroleum ether, dried
  10. filtrationover filter funnel in vacuo
  11. customto give

Sources & evidence

ORD record
ord-518a5fe586e04fdd8d81086627e8f87a
Source dataset
uspto-grants-2015_01
Patent number
US08933076B2

Reaction notes

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