Sodium hydride → HCID 83039773, compound

Participants

Reaction Steps

A −20° C. solution of 1-(2-chloroethyl)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)urea (0.700 g, 2.98 mmol) in THF (15 mL), under Ar, was treated with NaH (60% in mineral oil, 0.298 g, 7.46 mmol), allowed to warm to RT as the cooling bath expired and stirred overnight. The mixture was cooled to 0° C., quenched with saturated NH4Cl, warmed to RT, treatd with brine, extracted with EtOAc (2×) and the combined organics were dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-(2,2-dimethyltetrahydro-2H-pyran-4-yl)imidazolidin-2-one as a white solid (155 mg, 26%). 1H NMR (400 MHz, DMSO-d6): δ 6.24 (s, 1 H), 3.85 (m, 1 H), 3.67-3.54 (m, 2 H), 3.26-3.13 (m, 4 H), 1.53-1.37 (m, 4 H), 1.14 (d, J=10.2 Hz, 6 H); MS (ESI) m/z: 199.2 (M+H+).

Provenance & Evidence