4-Aminopyridine → 3-(Methylsulfanyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carbonitrile

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Reaction Steps

4-aminopyridine (930 mg, 9.9 mmol) is dissolved in anhydrous THF (30 mL) and potassium tertbutoxide (1.11 g, 9.9 mmol) is added. The resulting solution is stirred for 1 hour at room temperature. 3,5-Bis-methylsulfanyl-isothiazole-4-carbonitrile (6) (1.0 g, 4.94 mmol) is added and the reaction is stirred for 3 days. Ammonium chloride (173 mg, 9.9 mmol) is added and the resulting suspension is stirred at room temperature for 30 min. A small amount of water is added and the solution is filtered. The mother liquor is concentrated in vacuo. Chromatography (5% MeOH/methylene chloride) provides 7 (1.0g, 81%). 1H NMR (d6 DMSO): δ 8.29 (2H, broad s), 7.04 (2H, broad s), 2.60 (3H, s).

Provenance & Evidence