Diisopropylethylamine → HCID 68686581, compound

Participants

Reaction Conditions

Reaction Steps

2,4-dichloro-5-nitropyrimidine (Aldrich; 10 g, 0.052 mol) was dissolved in THF (250 mL). To this was added DIPEA (11 mL, 0.062 mol) and the reaction cooled to 0° C. Methyl3-(cyclohexylamino)propanoate (9.5 g, 0.052 mol) in THF (30 mL) was slowly added. The cooling bath was removed and the reaction was stirred at room temperature for 1 hour. To the reaction mixture was added saturated NH4OH(aq) (100 mL), and the reaction heated at 55° C. for 4 hours using a dry ice condenser. The reaction mixture was extracted with DCM (3×100 ml), and combined organic extracts dried and evaporated. The residue was dissolved in methanol (200 mL). Ammonium formate (33 g, 0.52 mol) and 10% palladium (1.5 g) were added. The reaction was heated at reflux for 5 hours, filtered and the methanol evaporated to yield a dark orange solid, which was quenched with 2.0 N NaOH(aq) (100 mL), extracted with DCM (3×150 mL), and combined extracts dried and evaporated to yield an orange solid. Hot acetonitrile was added, this was stirred and then sonicated to give a precipitate that was filtered and dried to yield the title compound as a yellow solid (7.5 g, 55%).

Provenance & Evidence