Cesium carbonate → 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Participants

Reaction Conditions

Reaction Steps

To a 35 ml sealed tube, 1-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one (2.0 g, 0.0048 mole) and (4-aminophenyl)methanol (0.78 g, 0.0063 mole) was taken in toluene (20.0 ml). The reaction mixture was purged with argon for 15 min at RT followed by Cs2CO3 (4.7 g, 0.0144 mole) was added and further purged for 30 min with argon. BINAP (0.06 g, 0.0001 mole) and Pd(OAc)2 (0.021 g, 0.0001 mole) were added to reaction mixture and heated to 110° C. for 4 hr. After completion of the reaction, the reaction mixture was filtered through celite bed and washed with ethyl acetate. Filtrate was collected and concentrated to afford crude product which was subjected for the column purification. The reaction with repeated twice and the crude product from each reaction was mixed and then purified using column purification by eluting the compound with 25-30% ethyl acetate in hexanes to yield 4.7 g of 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one.

Provenance & Evidence