Sodium hydride → HCID 67385015, compound

Participants

Reaction Steps

To a DMF solution (2 ml) of ice-cooled bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (80.0 mg, 0.148 mmol), 60% oily NaH (18 mg) was added, followed by stirring at room temperature for 15 minutes. To the reaction mixture, 2-chlorophenylisocyanate (53.4 μl, 0.445 mmol) was added, followed by further stirring for 1 hour. The reaction mixture was ice-cooled, and quenched with water (1 ml). This was diluted with dichloromethane (10 ml), and washed with water (10 ml×2). After the organic layer was dried over sodium sulfate, the sodium sulfate was filtered off, and the filtrate was concentrated under reduced pressure, to obtain a crude product 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 (2-chloro-phenyl)-amide as a brown solid (115 mg), and then the PMB groups were removed according to the above Deprotection method 3, to obtain the desired compound (D-217) as a colorless powder (39.2 mg, 58%).

Provenance & Evidence