Borohydride → HCID 59239060, compound

Participants

Reaction Steps

To a suspension of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea hydrochloride (ca) (174 mg, 0.4 mmol) and tetrahydrofuran-3-carbaldehyde (55 μL, 0.6 mmol) in THF (3 mL) was added Na(OAc)3BH in portions. After 2 hrs, more aldehyde (18 μL) and borohydride (71 mg) were added, and the resultant mixture was stirred for 1 h. The reaction mixture was quenched by addition of MeOH and few drops of AcOH, and concentrated in vacuo. The crude solid was redissolved in H2O, extracted with EtOAc (4×10 mL). The combined EtOAc were dried over Magnesium sulfate, filtered, and purified by RP-HPLC to afford 110 mg (57%) of compound ng as a yellow solid. 1H NMR (400 MHz, DMSO) δ 8.65 (s, 1H), 8.15 (d, J=8.8, 2H), 7.47 (d, J=8.8, 2H), 6.16 (t, J=5.5, 1H), 4.13 (d, J=6.6, 1H), 3.87 (d, J=11.3, 1H), 3.80-3.39 (m, 12H), 3.16-3.07 (m, 2H), 2.75-2.64 (m, 3H), 2.55 (d, J=8.6, 1H), 2.46 (d, J=7.4, 2H), 1.98 (td, J=12.7, 7.7, 1H), 1.57 (td, J=13.5, 7.1, 1H), 1.24 (d, J=6.6, 3H), 1.06 (t, J=7.2, 3H). LC-MS: m/z=+481 (M+H)+.

Provenance & Evidence