ethyl 4-amino-1-methylcyclohexane-1-carboxylate

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

Procedure: To an ice-cold solution of ethyl 4-amino-1-methylcyclohexanecarboxylate (0.18 g, 0.97 mmol) in EtOH (5.0 mL) was added DIPEA (0.52 mL, 2.91 mmol) followed by the addition of 5-bromo-2-chloropyrimidine (0.185 g, 0.97 mmol). The mixture was heated to 80° C. for 6-8 h after then cooled to rt, water added and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 4% EtOAc:hexane to obtain the desired product (0.064 g, 19%). MS: 342.01 [M+H]+. after then cooled to rt extracted with EtOAc (3×100 mL) The combined organics were washed with brine dried over anhydrous Na2SO4 filtered evaporated under reduced pressure The crude residue was purified over 100-200 M silica-gel

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

Procedure: To an ice-cold solution of ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate (0.30 g, 0.95 mmol) in EtOH (20 mL) was added hydrazine hydrate (0.115 mL, 2.38 mmol) and the resulting mixture heated up to 80° C. for 2-3 h. After the completion of reaction (by TLC), solvent was evaporated under reduced pressure, water added (20 mL), extracted with EtOAc (3×50 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product as a viscous liquid (0.18 g, crude). MS: 186.20 [M+H]+. After the completion of reaction (by TLC), solvent was evaporated under reduced pressure, water added (20 mL) extracted with EtOAc (3×50 mL) the combined organics washed with brine dried (Na2SO4) filtered concentrated under reduced pressure

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

Procedure: To an ice-cold solution of ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate (0.30 g, 0.95 mmol) in EtOH (20 mL) was added hydrazine hydrate (0.115 mL, 2.38 mmol) and the resulting mixture heated up to 80° C. for 2-3 h. After the completion of reaction (by TLC), solvent was evaporated under reduced pressure, water added (20 mL), extracted with EtOAc (3×50 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product as a viscous liquid (0.18 g, crude). MS: 186.20 [M+H]+. After the completion of reaction (by TLC), solvent was evaporated under reduced pressure, water added (20 mL) extracted with EtOAc (3×50 mL) the combined organics washed with brine dried (Na2SO4) filtered concentrated under reduced pressure

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

Procedure: To an ice-cold solution of ethyl 4-amino-1-methylcyclohexanecarboxylate (0.18 g, 0.97 mmol) in EtOH (5.0 mL) was added DIPEA (0.52 mL, 2.91 mmol) followed by the addition of 5-bromo-2-chloropyrimidine (0.185 g, 0.97 mmol). The mixture was heated to 80° C. for 6-8 h after then cooled to rt, water added and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 4% EtOAc:hexane to obtain the desired product (0.064 g, 19%). MS: 342.01 [M+H]+. after then cooled to rt extracted with EtOAc (3×100 mL) The combined organics were washed with brine dried over anhydrous Na2SO4 filtered evaporated under reduced pressure The crude residue was purified over 100-200 M silica-gel

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

Procedure: To an ice-cold solution of ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate (0.30 g, 0.95 mmol) in EtOH (20 mL) was added hydrazine hydrate (0.115 mL, 2.38 mmol) and the resulting mixture heated up to 80° C. for 2-3 h. After the completion of reaction (by TLC), solvent was evaporated under reduced pressure, water added (20 mL), extracted with EtOAc (3×50 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product as a viscous liquid (0.18 g, crude). MS: 186.20 [M+H]+. After the completion of reaction (by TLC), solvent was evaporated under reduced pressure, water added (20 mL) extracted with EtOAc (3×50 mL) the combined organics washed with brine dried (Na2SO4) filtered concentrated under reduced pressure