Methyl iodide → 2-Methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine
Reaktionsgleichung
[NH2:1][C:2]1[C:3]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[C:10]([CH3:20])[S:9][C:4]=2[NH:5][C:6](=[O:8])[CH:7]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:20][C:10]1[S:9][C:4]2[N:5]=[C:6]([O:8][CH3:21])[CH:7]=[C:2]([NH2:1])[C:3]=2[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a suspension of 4-amino-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-6(7H)-one (Description 36) (120 mg, 0.419 mmol) in DMF (3 mL) was added potassium carbonate (116 mg, 0.838 mmol) and methyl iodide (0.029 mL, 0.461 mmol). The suspension was then heated to 90° C. under nitrogen atmosphere for ca. 2 hand then cooled to RT, quenched with water (ca. 25 mL) and extracted with ethyl acetate (ca. 25 mL×2). The combined organic layers were passed through a phase separator and solvent concentrated in vacuo. The residue was purified by normal phase chromatography, eluting with a gradient of 0-100% ethyl acetate in DCM followed by 0-20% MeOH in DCM, to afford the title compound (16.5 mg). LCMS (A) m/z: 301 [M+1]+, Rt 1.21 min (acidic).
Aufarbeitung
- temperaturethen cooled to RT
- customquenched with water (ca. 25 mL)
- extractionextracted with ethyl acetate (ca. 25 mL×2)
- concentrationconcentrated in vacuo
- customThe residue was purified by normal phase chromatography
- washeluting with a gradient of 0-100% ethyl acetate in DCM
Quellen und Nachweise
- ORD-Eintrag
- ord-ac98575473d0415792aef8c2702d2b2e
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09029545B2
Notizen zur Reaktion
Wird geladen…