3-[2-(methoxymethyl)pyrrolidin-1-yl]aniline

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

Procedure: A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (170 mg, 0.83 mmol), 3-(2-(methoxymethyl)pyrrolidin-1-yl)aniline (170 mg, 0.83 mmol) and DIEA (214 g, 1.66 mmol) in 15 mL of DMSO was stirred at room temperature overnight. 100 mL of water were added, the mixture was extracted with ethyl acetate (3×30 mL). The organic layer was washed with water (2×30 mL) and brine (30 mL), concentrated under reduced pressure to give 5-chloro-N-(3-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 64%) as a yellow solid. LC-MS: 376 [M+H]+, tR=1.75 min. the mixture was extracted with ethyl acetate (3×30 mL) The organic layer was washed with water (2×30 mL) and brine (30 mL) concentrated under reduced pressure

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

Procedure: The mixture of 2-(methoxymethyl)-1-(3-nitrophenyl)pyrrolidine (200 mg, 0.85 mmol), Pd/C (50 mg, 10%) in 50 mL of MeOH was stirred at room temperature for 18 hours under H2 atmosphere. Pd/C was filtrated off and the filtrate was concentrated under reduce pressure to give crude 3-(2-(methoxymethyl)pyrrolidin-1-yl)aniline (170 mg) as an oil. LC-MS: 207 [M+H]+, tR=1.15 min. Pd/C was filtrated off the filtrate was concentrated