N1-(4-chlorophenyl)-6-methylisoquinoline-1,5-diamine → HCID 178422908, compound

Participants

Reaction Conditions

Reaction Steps

In a 2 mL microwave reaction tube were added 6-(4-chloropyrimidin-5-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (31 mg, 98 mop and N1-(4-chlorophenyl)-6-methylisoquinoline-1,5-diamine (28 mg, 98 μmol) in DMF (0.6 mL). The mixture was thoroughly mixed and flushed with argon then sealed. It was stirred at 70° C. The temperature was raised to 90° C. after 2 hrs and allowed over night. The reaction mixture was partitioned in EtOAc and NaHCO3. The organic layer was washed with brine and dried over Na2SO4. The residue was treated with MeOH (3 mL) and conc HCl (0.2 mL). The mixture was stirred for 2 hrs, then partitioned between NaHCO3 and EtOAc (10 mL each). The organic layer was collected and purified by prep HPLC (MeCN/H2O=5-95% with 0.1% TFA). Desired fractions were combined and neutralized with NaHCO3 (sat., aq.) and extracted with DCM. The DCM layer was washed with brine then dried over Na2SO4, then dried over a stream of N2 to give a yellow solid N5-(5-(9H-purin-6-yl)pyrimidin-4-yl)-N1-(4-chlorophenyl)-6-methylisoquinoline-1,5-diamine. MS Found: (ESI pos. ion) m/z 480 (M+H+).

Provenance & Evidence