2-ethylbenzenethiol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (0.09 g of 60% in oil) is added to 2-ethylthiophenol (0.26 g) in tetrahydrofuran (10 mL) and stirred for 15 minutes. N-(6-chloro-5-nitro-quinolin-8-yl)-acetamide (Gilman H., et al., Journal of American Chemical Society, 1946;66:1577) (0.5 g) is added and the mixture stirred at room temperature for 12 hours. The mixture is added to water (150 mL) and extracted with ethyl acetate (3×100 mL). The extracts are washed with saturated brine (150 mL), dried over magnesium sulfate, filtered, and evaporated to leave an oil. The oil is purified by chromatography on silica gel eluting with 50% ethyl acetate/hexane to give the title compound as a yellow solid. the mixture stirred at room temperature for 12 hours extracted with ethyl acetate (3×100 mL) The extracts are washed with saturated brine (150 mL) dried over magnesium sulfate filtered evaporated to leave an oil The oil is purified by chromatography on silica gel eluting with 50% ethyl acetate/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (0.09 g of 60% in oil) is added to 2-ethylthiophenol (0.26 g) in tetrahydrofuran (10 mL) and stirred for 15 minutes. N-(6-chloro-5-nitro-quinolin-8-yl)-acetamide (Gilman H., et al., Journal of American Chemical Society, 1946;66:1577) (0.5 g) is added and the mixture stirred at room temperature for 12 hours. The mixture is added to water (150 mL) and extracted with ethyl acetate (3×100 mL). The extracts are washed with saturated brine (150 mL), dried over magnesium sulfate, filtered, and evaporated to leave an oil. The oil is purified by chromatography on silica gel eluting with 50% ethyl acetate/hexane to give the title compound as a yellow solid. the mixture stirred at room temperature for 12 hours extracted with ethyl acetate (3×100 mL) The extracts are washed with saturated brine (150 mL) dried over magnesium sulfate filtered evaporated to leave an oil The oil is purified by chromatography on silica gel eluting with 50% ethyl acetate/hexane

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-{2-[4-(5-iodothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethyl-imidazolidine-2,4-dione (50 mg, 0.109 mmol) and 0.060 mL (0.44 mmol) of 2-ethylthiophenol in 2 mL toluene was treated with 3 mg of Pd2dba3 (0.003 mmol), 3 mg of Xantphos (0.005 mmol) and 0.22 mL of a 1 M solution of tBuOK in t-butanol. The reaction vial was sealed and heated at 110° C. in a microwave for 10 min. The crude solution was concentrated onto 5 g of silica gel and then purified by flash chromatography to give the title compound. MS (M+H)+ 468. The reaction vial was sealed The crude solution was concentrated onto 5 g of silica gel purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-{2-[4-(5-iodothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethyl-imidazolidine-2,4-dione (50 mg, 0.109 mmol) and 0.060 mL (0.44 mmol) of 2-ethylthio-phenol in 2 mL toluene was treated with 3 mg of Pd2 dba3 (0.003 mmol), 3 mg of Xantphos (0.005 mmol) and 0.22 mL of a 1 M solution of tBuOK in t-butanol. The reaction vial was sealed and heated at 110° C. in a microwave for 10 min. The crude solution was concentrated onto 5 g of silica gel and then purified by flash chromatography to give the title compound. MS (M+H)+ 468. The reaction vial was sealed The crude solution was concentrated onto 5 g of silica gel purified by flash chromatography