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

HRID 1784690ノート

反応式

HRID 1784690 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-81d542686bc54120bf1adf8893b40a75
出典データセット
uspto-grants-2009_03
特許番号
US07504411B2

反応ノート

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