2-甲苯基甲硫醇

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (200 mg, 1.002 mmol) and o-tolylmethanethiol (166 mg, 1.202 mmol) in tetrahydrofuran (THF) (5 mL) stirred in air at room temperature was added potassium tert-butoxide (112 mg, 1.002 mmol) in one charge. The reaction mixture was stirred at rt for 3 hr. The resulting mixture was concentrated and purified by prep-HPLC to give 50 mg 1-methyl-8-((2-methylbenzyl)thio)-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (50 mg, 0.158 mmol, 15.73% yield). charge The reaction mixture was stirred at rt for 3 hr The resulting mixture was concentrated purified by prep-HPLC

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In a manner similar to that described in Example 1A, 2-methylbenzylmercaptan is reacted with 17β-methanesulfonyloxy-1,4-androstadiene-3,11-dione to obtain the title compound of this example.

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-fluoro-benzaldehyde (1.16 g, 9.32 mmol) was added dropwise over 2 minutes to a solution of o-tolyl-methanethiol (1.35 g, 9.79 mmol) and Cesium carbonate (3.19 g, 9.79 mmol) in DMF (20 mL). The solution was stirred at 40° C. overnight and then poured into copious water. The pH of the solution was adjusted to 4 with 1N HCl(aq), and the aqueous solution was extracted with ethyl acetate (2×35 mL). The combined organic layers were washed with water, followed by brine. The combined organic layers were then dried (Na2SO4) and the solvent removed under reduced pressure. The resulting residue was purified via radial chromatography (15% ethyl acetate in hexanes) to yield 1.29 g (54%) of 4-(2-Methyl-benzylsulfanyl)-benzaldehyde (28.1). LC/MSD mle: 243.0 (M+H). the aqueous solution was extracted with ethyl acetate (2×35 mL) The combined organic layers were washed with water The combined organic layers were then dried (Na2SO4) the solvent removed under reduced pressure The resulting residue was purified via radial chromatography (15% ethyl acetate in hexanes)

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-fluoro-benzaldehyde (1.16 g, 9.32 mmol) was added dropwise over 2 minutes to a solution of o-tolyl-methanethiol (1.35 g, 9.79 mmol) and Cesium carbonate (3.19 g, 9.79 mmol) in DMF (20 mL). The solution was stirred at 40° C. overnight and then poured into copious water. The pH of the solution was adjusted to 4 with 1N HCl(aq), and the aqueous solution was extracted with ethyl acetate (2×35 mL). The combined organic layers were washed with water, followed by brine. The combined organic layers were then dried (Na2SO4) and the solvent removed under reduced pressure. The resulting residue was purified via radial chromatography (15% ethyl acetate in hexanes) to yield 1.29 g (54%) of 4-(2-Methyl-benzylsulfanyl)-benzaldehyde (28.1). LC/MSD m/e: 243.0 (M+H). the aqueous solution was extracted with ethyl acetate (2×35 mL) The combined organic layers were washed with water The combined organic layers were then dried (Na2SO4) the solvent removed under reduced pressure The resulting residue was purified via radial chromatography (15% ethyl acetate in hexanes)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (200 mg, 1.002 mmol) and o-tolylmethanethiol (166 mg, 1.202 mmol) in tetrahydrofuran (THF) (5 mL) stirred in air at room temperature was added potassium tert-butoxide (112 mg, 1.002 mmol) in one charge. The reaction mixture was stirred at rt for 3 hr. The resulting mixture was concentrated and purified by prep-HPLC to give 50 mg 1-methyl-8-((2-methylbenzyl)thio)-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (50 mg, 0.158 mmol, 15.73% yield). charge The reaction mixture was stirred at rt for 3 hr The resulting mixture was concentrated purified by prep-HPLC