Chloroform → HCID 67385775, compound

Participants

Reaction Steps

A toluene solution (60 ml) of {5-[7-(6-chloro-pyridin-3-yl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl}-bis-(4-methoxy-benzyl)-amine (200 mg, 0.30 mmol) obtained in Step A, N,N,N′-trimethyl ethylenediamine (60 μl, 46 mmol), Pd2(dba)3.CHCl3 (20 mg, 0.019 mmol), sodium-tert-butoxide (44 mg, 0.45 mmol) and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (31 mg, 0.092 mmol) was degassed under ultrasonic irradiation, followed by refluxing for 14 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and diluted with water, followed by extraction with dichloromethane. The organic layer was dried over magnesium sulfate, and subsequently magnesium sulfate was filtered off. Subsequently, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1), to obtain a crude product of N-[5-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-pyridin-2-yl]-N,N′,N′-trimethyl-ethane-1,2-diamine as a pale yellow solid (110 mg). Then the PMB groups were removed according to the above Deprotection method 2, to obtain the desired compound as a yellow powder (40 mg, 54%).

Provenance & Evidence