Methyl iodide → HCID 118023275, compound

HRID 2171800Notes

Reaction equation

HRID 2171800 reaction equation
[CH:1]1([C:7]2[S:25][C:10]3[N:11]=[C:12]([CH3:24])[N:13]=[C:14]([CH2:15][NH:16][CH:17]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26]C#N.CI.CCN(C(C)C)C(C)C>O>[CH:1]1([C:7]2[S:25][C:10]3[N:11]=[C:12]([CH3:24])[N:13]=[C:14]([CH2:15][N:16]([CH3:26])[CH:17]4[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)[C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 118023506HCID 118023506, compound

Product 1

HCID 118023275HCID 118023275, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]cycloheptaneamine (132 mg) and CH3CN (3 mL) were added CH3I (100 μL) and DIPEA (200 μL), followed by stirring at room temperature for 15 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by silica gel column (hexane/EtOAc) to obtain N-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]-N-methylcycloheptaneamine (77 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-09a32cecacc842fd8b462fe73510cb32
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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