Sodium Carbonate → HCID 68379371, compound

Participants

Reaction Steps

To a solution of (S)-5-chloro-N-(3-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 0.58 mmol) and crude tert-butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylamino)piperidine-1-carboxylate in 10 mL of 1,4-dioxane and 2 mL of water was added Na2CO3 (184 mg, 1.74 mmol) followed by Pd(PPh3)4 (184 mg, 0.03 mmol) under nitrogen with stirring. The mixture was refluxed for 15 hours under nitrogen. After cooled, the solvent was evaporated by rotary evaporation under reduced pressure. The residue was poured into water and extracted with EtOAc (3×15 mL). The organic layer was washed with brine and dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography (silica gel, eluting with EtOAc) to give (S)-tert-butyl 4-(3-(7-(3-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzylamino)piperidine-1-carboxylate (110 mg, 32% for the two steps). LC-MS: 250.6 [M/2+H]+, 600 [M+H]+, tR=1.57 min.

Provenance & Evidence