Methyl iodide → N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-N-methyltetrahydro-2H-thiopyran-4-amine 1,1-dioxidehydrochloride

HRID 2171824Notes

Reaction equation

HRID 2171824 reaction equation
[ClH:1].[CH3:2][C:3]1([CH3:29])[CH2:8][CH2:7][CH:6]([C:9]2[S:28][C:12]3[N:13]=[C:14]([CH3:27])[N:15]=[C:16]([CH2:17][NH:18][CH:19]4[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]4)[C:11]=3[CH:10]=2)[CH2:5][CH2:4]1.CI.[C:32]([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CN(C=O)C>[ClH:1].[CH3:2][C:3]1([CH3:29])[CH2:4][CH2:5][CH:6]([C:9]2[S:28][C:12]3[N:13]=[C:14]([CH3:27])[N:15]=[C:16]([CH2:17][N:18]([CH3:32])[CH:19]4[CH2:20][CH2:21][S:22](=[O:25])(=[O:26])[CH2:23][CH2:24]4)[C:11]=3[CH:10]=2)[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 118023896N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}tetrahydro-2H-thiopyran-4-amine-1,1-dioxide hydrochloride

Product 1

HCID 118023764N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-N-methyltetrahydro-2H-thiopyran-4-amine 1,1-dioxidehydrochlorideYield 66.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}tetrahydro-2H-thiopyran-4-amine-1,1-dioxide hydrochloride (100 mg), CH3I (16 μL) and DMF (2.0 mL) was added K2CO3 (60 mg), followed by stirring at 50° C. overnight. The reaction mixture was left to be cooled, and a saturated aqueous NH4Cl solution was added thereto, followed by extraction with EtOAc. The organic layer was washed sequentially with water and brine, and dried over MgSO4. The residue was purified by silica gel column. The obtained purified product was dissolved in EtOAc, and 4 M HCl/EtOAc (55 μL) was added dropwise thereto. The precipitate was collected by filtration and then dried to obtain N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-N-methyltetrahydro-2H-thiopyran-4-amine 1,1-dioxidehydrochloride (69 mg).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. extractionfollowed by extraction with EtOAc
  4. washThe organic layer was washed sequentially with water and brine
  5. dry with materialdried over MgSO4
  6. customThe residue was purified by silica gel column
  7. customThe obtained purified product
  8. dissolutionwas dissolved in EtOAc
  9. addition4 M HCl/EtOAc (55 μL) was added dropwise
  10. filtrationThe precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-64a0feef61864112b8eb81607bef8806
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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