Triethylamine → (S)-2-(3-(4-(N,N-dimethylamino)phenyl) piperazin-1-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-one trihydrochloride

HRID 1784690Notes

Reaction equation

HRID 1784690 reaction equation
[ClH:1].Cl.Cl.[CH3:4][N:5]([C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][NH:17][CH2:16][CH2:15][NH:14]2)=[CH:9][CH:8]=1)[CH3:6].C(N(CC)CC)C.[Cl:26][C:27]1[N:32]([CH3:33])[C:31](=[O:34])[CH:30]=[C:29]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[N:28]=1>O1CCCC1>[ClH:26].[ClH:1].[ClH:26].[CH3:6][N:5]([C:7]1[CH:8]=[CH:9][C:10]([C@@H:13]2[NH:14][CH2:15][CH2:16][N:17]([C:27]3[N:32]([CH3:33])[C:31](=[O:34])[CH:30]=[C:29]([C:35]4[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=4)[N:28]=3)[CH2:18]2)=[CH:11][CH:12]=1)[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 67117392(S)-2-(4-(N,N-dimethylamino)phenyl)piperazine trihydrochloride

Product 1

HCID 53628947(S)-2-(3-(4-(N,N-dimethylamino)phenyl) piperazin-1-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-one trihydrochlorideYield 163.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (S)-2-(4-(N,N-dimethylamino)phenyl)piperazine trihydrochloride (115 mg, 0.365 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.28 mL, 2.0 mmol) and then 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (74 mg, 0.33 mmol) at room temperature. After stirring for 10 h, the resulting mixture was concentrated in vacuo. The residue was dissolved in dichloromethane and saturated sodium bicarbonate aqueous solution, and the solution was passed through CHEM ELUT CE1010 (manufactured by VARIAN). The filtrate was concentrated in vacuo to yield crystals, which were washed with diisopropyl ether. After the crystals were dissolved in ethyl acetate, the solution was treated with 4 N hydrogen chloride in ethyl acetate. White precipitate was collected and dried in vacuo to afford (S)-2-(3-(4-(N,N-dimethylamino)phenyl) piperazin-1-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-one trihydrochloride (135 mg, 81%).

Workup

  1. customat room temperature
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto yield crystals, which
  6. washwere washed with diisopropyl ether
  7. dissolutionAfter the crystals were dissolved in ethyl acetate
  8. additionthe solution was treated with 4 N hydrogen chloride in ethyl acetate
  9. customWhite precipitate was collected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-81d542686bc54120bf1adf8893b40a75
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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