3-[(2S)-2-methylpyrrolidin-1-yl]aniline

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

Procedure: A mixture of (S)-3-(2-methylpyrrolidin-1-yl)benzenamine (0.9 g, 5.34 mmol), 5,7-dichlorothiazolo[5,4-d]pyrimidine (1.1 g, 5.34 mmol), DIEA (1.4 g, 10.68 mmol) in IPA (15 mL) was heated to reflux for 2 hours. Then the reaction mixture was concentrated and residue purified by column chromatography (petroleum ether:ethyl acetate=8:1) to give (S)-5-chloro-N-(3-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (1.6 g, 91.4%) as yellow solid. LC-MS: 346 [M+H]+, tR=1.82 min. was heated to reflux for 2 hours Then the reaction mixture was concentrated residue purified by column chromatography (petroleum ether:ethyl acetate=8:1)

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

Procedure: A mixture of (S)-2-methyl-1-(3-nitrophenyl)pyrrolidine (1.1 g, 5.34 mmol) and Pd/C (0.2 g) in MeOH (50 mL) was purged with H2 then stirred for 16 hours under H2 atmosphere. Catalyst was removed by filtration and filtrate concentrated to give crude (S)-3-(2-methylpyrrolidin-1-yl)benzenamine (1 g, 100%), used into the next step without further purification. LC-MS: 177 [M+H]+, tR=1.09 min. was purged with H2 Catalyst was removed by filtration and filtrate concentrated