HCID 68295331, compound → HCID 60198962, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-(3,4-dichlorophenyl)-3-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)propylcarbamate (89 mg, 0.17 mmol) in THF (5 mL) under N2 was added BH3.THF complex (0.36 mL, 0.36 mmol) and the reaction was heated at reflux under N2 for 19 h. The reaction was cooled to RT, quenched with MeOH (10 mL), and heated at reflux for 1 h. The reaction was concentrated, then partitioned between DCM (25 mL) and sat. aq. NaHCO3 (25 mL). The phases were separated, the aqueous phase extracted with DCM (25 ml). The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified on a preparative SiO2 TLC (1 mm) plate developed with MeOH/DCM/NH4OH (9/90/1) to afford 11 mg (15%) of I-111 as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.36 (m, 2H), 7.13 (dd, 1H), 4.91 (m, 1H), 4.80 (d, 1H), 4.37 (m, 2H), 4.10 (m, 1H), 3.69 (m, 1H), 3.61 (m, 1H), 2.64-2.75 (m, 4H), 2.48 (s, 3H), 2.02 (m, 1H), 1.73 (m, 1H), 1.22 (dd, 6H); LRMS (APCI pos) m/e=451.1 (M+H).

Provenance & Evidence