Triethylamine → 2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-N-methoxy-N-ethyl-acetamide

Participants

Reaction Steps

A mixture of (2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid (722 mg, 2.34 mmol) and CDI (493 mg, 3.04 mmol) in DCM (5 mL) was stirred at RT for 1.5 hours before the addition of triethylamine (457 μL, 3.28 mmol) and O,N-dimethyl-hydroxylamine hydrochloride (320 mg, 3.28 mmol). The resulting mixture was stirred for 18 hours then quenched with 1M HCl. The aqueous layer was extracted with DCM and the combined organic extracts were washed with brine, then dried (Na2SO4) and concentrated in vacuo to afford 2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-N-methoxy-N-ethyl-acetamide as a yellow oil (830 mg, quantitative). LCMS: RT=2.83 min, [M+H]+=351/353/355.

Provenance & Evidence