Tetrahydrofuran → HCID 66600042, compound

Participants

Reaction Conditions

Reaction Steps

To a 15 mL round-bottomed flask was added 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)nicotinaldehyde (0.438 g, 0.735 mmol), (R)-tert-butyl 2-methylpiperazine-1-carboxylate (0.368 g, 1.838 mmol), tetrahydrofuran (0.053 g, 0.735 mmol), titanium (iv) ethoxide (0.761 mL, 3.68 mmol) (Aldrich). The flask was sealed and the solution was stirred at 70° C. overnight. The solution was stirred at 0° C. and treated in one portion with sodium cyanotrihydridoborate (0.462 g, 7.35 mmol) (Aldrich). The suspension was stirred at 0° C. for two hours. The suspension was quenched with drops of MeOH and water, then DCM. The suspension was stirred for 10 minutes vigorously and was filtered through Celite® (diatomaceous earth) and the filtrated cake was washed with DCM. The organic phase was concentrated to afford (R)-tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-2-methylpiperazine-1-carboxylate (0.425 g, 0.545 mmol, 74.1% yield).

Provenance & Evidence