Dimethylformamide → HCID 59239453, compound

Participants

Reaction Conditions

Reaction Steps

and 1-(4-((S)-8-(cyanomethyl)-7-isopropyl-4-((S)-3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (xu2): 1-(4-(8-(cyanomethyl)-4-((S)-3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (0.0947 g, 0.217 mmol) in dry N,N-Dimethylformamide (1.600 mL, 20.66 mmol) was added N,N-Diisopropylethylamine (0.1200 mL, 0.6888 mmol) followed by Isopropyl iodide (0.0460 mL, 0.460 mmol). The reaction mixture was heated at 50° C. and stirred overnight. The reaction mixture was heated at 80° C. and stirred overnight. The reaction mixture was heated at 90° C. overnight. Added Isopropyl iodide (0.1150 mL, 1.150 mmol) and N,N-Diisopropylethylamine (0.1200 mL, 0.6889 mmol). The reaction mixture was heated at 120° C. and stirred for 4 days. The reaction mixture was concentrated and chromatographed through silica gel (40 g, 0-5% MeOH in dichloromethane), purified by HPLC, and the diastereomers were separated out by SFC. Diastereomer 1 LC/MS-m/z+478.3 (M+H)+; Diastereomer 2 LC/MS-m/z+478.2 (M+H)+.

Provenance & Evidence