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 2171824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171824
[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

Komponenten

6

Edukt 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

Produkt 1

HCID 118023764N-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}-N-methyltetrahydro-2H-thiopyran-4-amine 1,1-dioxidehydrochlorideAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-64a0feef61864112b8eb81607bef8806
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051339B2

Notizen zur Reaktion

Wird geladen…