1-(2-Hydroxyethyl)piperazine → 4-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {3-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-phenyl}-methyl-amide

Participants

Reaction Conditions

Reaction Steps

To a DMF solution (2.0 ml) of 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (3-bromo-phenyl)-methyl-amide (70.5 mg) obtained in Step B, tris(dibenzylideneacetone) dipalladium (4.3 mg), S-Phos (3.8 mg) and potassium phosphate (39.8 mg), 2-piperazin-1-yl-ethanol (23 μl) was added, and degassed under ultrasonic irradiation. After this was stirred at 100° C. for 4 hours, water (10 ml) was added, followed by extraction with ethyl acetate (10 ml×2), and the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography, to obtain 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {3-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-phenyl}-methyl-amide. The PMB groups were removed according to Deprotection method 3, to obtain the desired compound (D-153) as a colorless solid (7.2 mg, 14%).

Provenance & Evidence