Pyridine → HCID 118024110, compound

HRID 2171822Notes

Reaction equation

HRID 2171822 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][CH:5]([C:8]2[S:25][C:11]3[N:12]=[C:13]([CH3:24])[N:14]=[C:15]([CH2:16][NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.C(Cl)Cl.[C:36](OC(=O)C)(=[O:38])[CH3:37]>O>[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][CH:5]([C:8]2[S:25][C:11]3[N:12]=[C:13]([CH3:24])[N:14]=[C:15]([CH2:16][N:17]([CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:36](=[O:38])[CH3:37])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 118023960HCID 118023960, compound

Product 1

HCID 118024110HCID 118024110, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}tetrahydro-2H-pyran-4-amine (60 mg), pyridine (129 μL), and DCM (1.8 mL) was added acetic anhydride (76 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 Na2SO4, and then concentrated under reduced pressure. The residue was purified by silica gel column to obtain N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-N-(tetrahydro-2H-pyran-4-yl)acetamide (23 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-ddb6b3bca846483283b06a4618475ff4
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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