3-(methylsulfanylmethyl)aniline

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 4N solution of hydrogen chloride in dioxane (0.61 mL; 2.45 mmol) was added to a stirred solution of 2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (630 mg; 2.45 mmol) and 3-[(methyl-sulfanyl)methyl]aniline (564 mg; 3.68 mmol) in 1-butanol (5.4 mL). The batch was stirred at 140° C. for 16 hours. After cooling the batch was diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic phase was filtered using a Whatman filter and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 2:1) to give the desired product (662 mg; 1.77 mmol). After cooling the batch washed with aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution The organic phase was filtered filter concentrated The residue was purified by chromatography (hexane/ethyl acetate 2:1)

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 4N solution of hydrogen chloride in dioxane (0.34 mL; 1.35 mmol) was added to a stirred solution of 4-[2-(benzyloxy)-4-fluorophenyl]-2-chloro-5-fluoropyrimidine (450 mg; 1.35 mmol) and 3-[(methylsulfanyl)methyl]aniline (311 mg; 2.03 mmol) in 1-butanol (3.00 mL). The batch was stirred at 140° C. for 16 hours. After cooling the batch was diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic phase was filtered using a Whatman filter and concentrated. The residue was purified by preparative HPLC to give the desired product (167 mg; 0.37 mmol). After cooling the batch washed with aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution The organic phase was filtered filter concentrated The residue was purified by preparative HPLC