HCID 9886228, compound → HCID 9969243, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(1-Ethyl-propyl)-4,7-dimethyl-5-(2,4,6-trimethyl-phenoxy)-1,4-dihydro-2H-pyrido[3,4-b]pyrazin-3-one (21 mg, 0.055 mmol) and 2 M borane dimethylsulfide complex (BH3•DMS) (0.07 ml, 0.14 mmol) in 2 ml of dry THF was heated at reflux for 3 hours. The mixture was cooled to 0° C. and quenched with 0.2 ml of meoh and 0.2 ml of concentrated hydrochloric acid (HCl). The resulting mixture was stirred at room temperature for 2 hours and concentrated to dryness. The residue was quenched with water and extracted with chloroform. The organic layer was dried and concentrated to give 19 mg of a clear oil that was purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 11 mg of the title compound as white crystals, mp 78-80° C.; 1H NMR (CDCl3) δ 6.85(s,2H), 6.28(s,1H), 3.73(m,1H), 3.12 (m,4H), 2.85(s,3H), 2.29(s,3H), 2.,13(s,3H), 2.11 (s,6H), 1.61(m,4H), 0.90(t,6H) ppm.

Provenance & Evidence