Formaldehyde → HCID 46913467, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (example 7) (150 mg, 0.36 mmol) in THF (3 mL) was added aqueous formaldehyde 37 Wt % (58 μL, 0.72 mmol) and Et3N (149 μL, 1.07 mmol). The reaction mixture was then stirred at room temperature (20° C.) for 1 h. After this time sodium triacetoxyborohydride (152 mg, 0.72 mmol) was added and stirring at room temperature (20° C.) continued for 18 h. The crude reaction mixture was then partitioned between water and EtOAc, the phases separated and the organic layer washed with NaHCO3 and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by prep HPLC (low pH) to give as a light brown solid (48 mg, 33%).

Provenance & Evidence