Potassium Phosphate, Tribasic → 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 (4-pyridin-3-yl-phenyl)-amide

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Reaction Steps

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 (4-iodo-phenyl)-amide (35 mg) obtained in Step A, pyridin-3-boronic acid (11 mg), palladium acetate (1.0 mg), S-Phos (3.7 mg) and potassium phosphate (9.5 mg) were stirred at 100° C. for 3 hours in DMF (4.5 ml). To this, water was added, and the solid was filtered, followed by purification by silica gel column chromatography (dichloromethane/methanol=100/1 to 50/1), 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 (4-pyridin-3-yl-phenyl)-amide as a crude product. To this, N-Acetylcysteine (11 mg) was added, followed by refluxing for 4 hours in TFA (1 ml). TFA was distilled off, followed by purification by silica gel column chromatography (dichloromethane/methanol=100/1 to 50/1), to obtain the desired compound (D-65) as a colorless solid (5.0 mg, 23%, deprotection method according to the above Deprotection method 3).

Provenance & Evidence