5-methyl-1,3-oxazolidin-2-one

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: A 3-dimethylsilyl-5-methyl-2-oxazolidinone was prepared in accordance with the following procedure. A stirred mixture of 60.6 grams of 5-methyl-2-oxazolidinone and 62.4 grams of triethylamine was prepared in a tetrahydrofuran solvent. To this mixture, 67.5 ml of dimethylchlorosilane was added dropwise over a period of 90 minutes.

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: By reaction and treatment in the same manner as in Example 1 and using (6-bromopyridin-3-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (93 mg) described in Preparation Example 73 and 5-methyloxazolidin-2-one (30 mg), the title compound (29 mg) was obtained. By reaction and treatment in the same manner as in Example 1

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

Procedure: A mixture of 1-amino-2-propanol (1.4 g), diethyl carbonate (2.4 mL) and potassium carbonate (500 mg) was stirred at 150° C. for 3 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give 5-methyloxazolidin-2-one (1.9 g). To a mixture of ethyl 4-iodobenzoate (3.2 mL), 5-methyloxazolidin-2-one (1.9 g), potassium carbonate (8 g) and copper (I) iodide (720 mg) were added toluene (20 mL) and N,N′-dimethylethylenediamine (800 μL), and the mixture was refluxed for 3 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was dissolved in methanol (20 mL) and 1,4-dioxane (20 mL), 1N aqueous sodium hydroxide solution (40 mL) was added, and the mixture was stirred at room temperature for 3 hr. 1N hydrochloric acid (40 mL) was added, and the mixture was extracted with chloroform. The solvent was evaporated to give the title compound (3.9 g). the mixture was refluxed for 3 hr After cooling the mixture was extracted with chloroform The organic layer was washed with saturated brine the solvent was evaporated The residue was dissolved in methanol (20 mL) 1,4-dioxane (20 mL), 1N aqueous sodium hydroxide solution (40 mL) was added 1N hydrochloric acid (40 mL) was added the mixture was extracted with chloroform The solvent was evaporated

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

Procedure: A 3-dimethylsilyl-5-methyl-2-oxazolidinone was prepared in accordance with the following procedure. A stirred mixture of 60.6 grams of 5-methyl-2-oxazolidinone and 62.4 grams of triethylamine was prepared in a tetrahydrofuran solvent. To this mixture, 67.5 ml of dimethylchlorosilane was added dropwise over a period of 90 minutes.