(2R)-2-ethylpyrrolidine

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2R)-2-ethylpyrrolidine (0.8 g, 5.90 mmol) and 4,6-dichloro-N-methyl-2-pyrimidinamine (0.997 g, 5.60 mmol) in 1,4-dioxane (40 mL) and saturated aqueous NaHCO3 (20 mL) was stirred overnight at 100° C. into a sealed tube. The reaction mixture was poured onto water (˜400 mL). A white precipitate was formed. The aqueous mixture was filtered, and the white solid was washed with water (˜100 mL). The wet solid was dried overnight on vacuum at 40° C. to afford the title compound (1.19 g). LC-MS (ES) m/z=241 [M+H]+. The reaction mixture was poured onto water (˜400 mL) A white precipitate was formed The aqueous mixture was filtered the white solid was washed with water (˜100 mL) The wet solid was dried overnight on vacuum at 40° C.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2R)-2-ethylpyrrolidine (0.8 g, 5.90 mmol) and 4,6-dichloro-N-methyl-2-pyrimidinamine (0.997 g, 5.60 mmol) in 1,4-dioxane (40 mL) and saturated aqueous NaHCO3 (20 mL) was stirred overnight at 100° C. into a sealed tube. The reaction mixture was poured onto water (˜400 mL). A white precipitate was formed. The aqueous mixture was filtered, and the white solid was washed with water (˜100 mL). The wet solid was dried overnight on vacuum at 40° C. to afford the title compound (1.19 g). LC-MS (ES) m/z=241 [M+H]+. The reaction mixture was poured onto water (˜400 mL) A white precipitate was formed The aqueous mixture was filtered the white solid was washed with water (˜100 mL) The wet solid was dried overnight on vacuum at 40° C.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2R)-2-ethylpyrrolidine (0.8 g, 5.90 mmol) and 4,6-dichloro-N-methyl-2-pyrimidinamine (0.997 g, 5.60 mmol) in 1,4-dioxane (40 mL) and saturated aqueous NaHCO3 (20 mL) was stirred overnight at 100° C. into a sealed tube. The reaction mixture was poured onto water (˜400 mL). A white precipitate was formed. The aqueous mixture was filtered, and the white solid was washed with water (˜100 mL). The wet solid was dried overnight on vacuum at 40° C. to afford the title compound (1.19 g). LC-MS (ES) m/z=241 [M+H]+. The reaction mixture was poured onto water (˜400 mL) A white precipitate was formed The aqueous mixture was filtered the white solid was washed with water (˜100 mL) The wet solid was dried overnight on vacuum at 40° C.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2R)-2-ethylpyrrolidine (80 mg, 0.59 mmol), 4,6-dichloro-2-pyrimidinamine (119 mg, 0.726 mmol) and Et3N (0.25 mL, 1.77 mmol) in CH3CN (6 mL) was stirred overnight at 80° C. The mixture was poured onto water (˜150 mL), sonicated and filtered to afford the title compound (94 mg, 70%) as a white solid. LC-MS (ES) m/z=227, 229 [M+H]+. The mixture was poured onto water (˜150 mL) sonicated filtered

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

Procedure: The title compound is prepared in a manner substantially analogous to Procedure RR starting from (2-(S)-hydroxymethyl-pyrrolidin-1-yl)-(4′-trifluoromethyl-biphenyl-4-yl)-methanone and 2-(R)-ethyl-pyrrolidine (CAS 460748-80-5) MS (M+H) 431.3.

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

Procedure: The title compound is prepared in a manner substantially analogous to Procedure RR starting from (2-(S)-hydroxymethyl-pyrrolidin-1-yl)-(4′-trifluoromethyl-biphenyl-4-yl)-methanone and 2-(R)-ethyl-pyrrolidine (CAS 460748-80-5) MS (M+H) 431.3.