Diisopropylethylamine → (S)-5-chloro-N-(3-methoxy-5-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

Participants

Reaction Conditions

Reaction Steps

The mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol), (S)-3-methoxy-5-(2-methylpyrrolidin-1-yl)benzenamine (220 mg, 1.07 mmol) and DIPEA (150 mg, 1.17 mmol) in DMSO (50 mL) was heated to 30° C. with stirring for 16 h. The mixture was diluted with water, extracted with ethyl acetate (50 mL), combined organics washed with water (10 mL×4) then brine (10 mL×2), dried over Na2SO4 and concentrated to give the residue which was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford (S)-5-chloro-N-(3-methoxy-5-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (280 mg, 77%) as yellow oil. LC-MS: 376 [M+H]+, tR=1.825 min.

Provenance & Evidence