Reaktionsgleichung
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.Br[CH2:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][CH:30]=1)[O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>>[Si:21]([O:20][C:19]1[CH:18]=[C:17]([CH:30]=[CH:29][CH:28]=1)[CH2:16][O:14][C:13]1[C:8]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)=[N:9][CH:10]=[CH:11][CH:12]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]Komponenten
4
Versuchsvorschrift
Following the method according to Example 3, Steps B and C, 5, 2-(4-methylthiazol-2-ylamino)pyridin-3-ol (prepared according to Example 3, Step A; 5.0 g, 24 mmol), (3-(bromomethyl)phenoxy)(tert-butyl)dimethylsilane (7.3 g, 24 mmol) [J. Med. Chem. (1992), 35, 3498] and potassium carbonate (8.3 g, 60 mmol) were combined to provide 3-(3-(tert-butyldimethylsilyloxy)benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (5.4 g, 48% yield) as a clear and colorless oil. 1H NMR (CDCl3) δ 8.61 (bs, 1H), 7.94 (dd, 1H), 7.26 (m, 1H), 7.06 (dd, 1H), 7.00 (m, 1H), 6.84 (m, 2H), 6.79 (dd, 1H), 6.38 (s, 1H), 5.06 (s, 2H), 2.33 (s, 3H), 0.97 (s, 9H), 0.20 (s, 6H). Mass spectrum (apci) m/z=428.2 (M+H).
Quellen und Nachweise
- ORD-Eintrag
- ord-af08e881f5d24cb8a35c4102059ae897
- Quelldatensatz
- uspto-grants-2015_01
- Patentnummer
- US08933077B2
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