Pyridine → HCID 118023386, compound

HRID 2171817Notes

Reaction equation

HRID 2171817 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:7][CH2:6][CH:5]([C:8]2[S:26][C:11]3[N:12]=[C:13]([CH3:25])[N:14]=[C:15]([CH2:16][N:17]4[CH2:22][CH2:21][NH:20][CH2:19][C:18]4([CH3:24])[CH3:23])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.C(Cl)[Cl:35].[C:37](OC(=O)C)(=[O:39])[CH3:38]>O>[ClH:35].[CH3:1][C:2]1([CH3:27])[CH2:7][CH2:6][CH:5]([C:8]2[S:26][C:11]3[N:12]=[C:13]([CH3:25])[N:14]=[C:15]([CH2:16][N:17]4[CH2:22][CH2:21][N:20]([C:37](=[O:39])[CH3:38])[CH2:19][C:18]4([CH3:23])[CH3:24])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 118024061HCID 118024061, compound

Product 1

HCID 118023386HCID 118023386, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6-(4,4-dimethylcyclohexyl)-4-[(2,2-dimethylpiperazin-1-yl)methyl]-2-methylthieno[2,3-d]pyrimidine (40 mg), pyridine (83 μL), and DCM (1.2 mL) was added acetic anhydride (49 μL), followed by stirring at room temperature for 30 minutes. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column. To a solution of the obtained purified product in EtOAc was added dropwise 4 M HCl/dioxane, and the precipitate was collected by filtration and dried to obtain 1-(4-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-3,3-dimethylpiperazin-1-yl)ethanone hydrochloride (35 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column
  6. customTo a solution of the obtained purified product in EtOAc
  7. additionwas added dropwise 4 M HCl/dioxane
  8. filtrationthe precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-67114f93963445d8af5bdac2f1341ac3
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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