4-methylpyrrolidin-2-one

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

Procedure: The product of EXAMPLE 180 is reacted with trimethyloxonium tetrafluoroborate by the method of EXAMPLE 26 to produce the title material.

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

Procedure: The product of EXAMPLE 180 is reacted with trimethyloxonium tetrafluoroborate by the method of EXAMPLE 26 to produce the title material.

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

Procedure: To a mixture of ethyl 4-iodobenzoate (552 mg), 4-methylpyrrolidin-2-one (198 mg), potassium carbonate (536 mg) and copper(I) iodide (190 mg) were added toluene (2 mL) and N,N′-dimethylethylenediamine (215 μL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (377 mg). with heating under reflux for 8 hr The reaction mixture was cooled the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine the solvent was evaporated The obtained residue was purified by column chromatography (hexane:ethyl acetate)

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

Procedure: To a mixture of ethyl 4-iodobenzoate (552 mg), 4-methylpyrrolidin-2-one (198 mg), potassium carbonate (536 mg) and copper(I) iodide (190 mg) were added toluene (2 mL) and N,N′-dimethylethylenediamine (215 μL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (377 mg). with heating under reflux for 8 hr The reaction mixture was cooled the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine the solvent was evaporated The obtained residue was purified by column chromatography (hexane:ethyl acetate)

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

Procedure: To a mixture of ethyl 4-iodobenzoate (552 mg), 4-methylpyrrolidin-2-one (198 mg), potassium carbonate (536 mg) and copper(I) iodide (190 mg) were added toluene (2 mL) and N,N′-dimethylethylenediamine (215 μL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (377 mg). with heating under reflux for 8 hr The reaction mixture was cooled the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine the solvent was evaporated The obtained residue was purified by column chromatography (hexane:ethyl acetate)

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a Schlenk tube (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (0.95 g), NaOtBu (0.29 g), dppf (0.1 g), Pd(OAc)2 (0.01 g) and 4-methylpyrrolidin-2one (0.2 g) are added: Three consecutive cycles of vacuum/argon are applied. Thereafter, 10 ml of degassed dioxane is added and the solution is heated to 120° C. (external temperature) for 8 hours. The solvent is removed under vacuum and the crude product is purified over column chromatography (eluent; EE/MeOH=9/1) yielding the title compound, m.p. 162–164° C. The solvent is removed under vacuum the crude product is purified over column chromatography (eluent; EE/MeOH=9/1)

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

Procedure: The product of EXAMPLE 180 is reacted with trimethyloxonium tetrafluoroborate by the method of EXAMPLE 26 to produce the title material.

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

Procedure: To a 100 ml flask containing 9.91 g of 4-methylpyrrolidone (0.1 mol), 30 ml benzene was added and stirred for dissolution. 11.40 g of trifluoroacetic acid (0.1 mol) was added dropwise into the flask over 40 min at room temperature. Then the reaction was stirred for another 6 hours. Desired product was formed after benzene was removed under reduced pressure and dried at 110° C. under 1–5 mmHg for 1 hour. The brown viscous, moisture- and water-stable liquid of 4-methylpyrrolidonium trifluoroacetate was obtained with a yield of 97.7%, which has a glass transition temperature of −85.0° C., a density of 1.33 g/ml, a viscosity of 22 cP, an electrochemical window of 2.4 V, an ionic conductivity of 5.63×10−4 S/cm, and a Hammett acidic scale H0 of 4.82 using methyl yellow as indicator. No melting point was observed. was added Then the reaction was stirred for another 6 hours

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

Procedure: The product of EXAMPLE 180 is reacted with trimethyloxonium tetrafluoroborate by the method of EXAMPLE 26 to produce the title material.

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

Procedure: The product of EXAMPLE 180 is reacted with trimethyloxonium tetrafluoroborate by the method of EXAMPLE 26 to produce the title material.