Sodium hydride → [4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-(5-phenyl-thiazol-2-yl)-amine

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Reaction Steps

4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamine (8-5), 1.00 g (4.19 mmol) was dissolved in 20 mL anhydrous THF at room temp, and NaH (60% dispersion, 0.670 g, 16.8 mmol) was added. When the bubbling stopped, 2-chloro-5-phenyl-thiazole (Hafez, E. A. A.; Abed, N. M.; Elsakka, I. A.; J. Heterocycl. Chem. 1983; 20, 285-288), 0.739 g (3.78 mmol) was added, and the reaction was heated to reflux. After 2 hours the THF was removed in vacuo and the resulting solution was taken to neutral pH with 1M HCl (aq) and filtered. The residue was purified by flash column chromatography using 20% EtOAc in hexane. 1H NMR (CDCl3): δ 9.09 (bs, 1H), 8.32 (d, 1H, J=5.2 Hz), 7.62 (s, 1H), 7.56 (d, 2H, J=7.4 Hz), 7.38 (t, 2H, J=7.6 Hz), 7.26 (overlapping with CHCl3, 1H), 6.90 (s, 1H), 6.82 (d, 1H, J=5.2 Hz), 4.75 (s, 2H), 0.96 (s, 9H), 0.14 (s, 6H). mp 207° C.

Provenance & Evidence