Sodium hydride → HCID 117653594, compound

Participants

Reaction Steps

A 5° C. solution of 1-(prop-2-yn-1-yl)-3-(tetrahydro-2H-pyran-4-yl)urea (0.40 g, 2.195 mmol) in THF (20 mL) under Ar, was treated with NaH (60% in mineral oil, 0.097 g, 2.415 mmol), warmed to RT and stirred overnight. The mixture was treated with satd. NH4Cl, extracted with EtOAc (2×) and the combined organics were washed with 5% LiCl, then brine and dried over Na2SO4. The solution was treated with Pd on C (260 mg) and hydrogenated (30 psi) for 5 h. The mixture was filtered, treated with fresh Pd on C (260 mg) and hydrogenated (44 psi) overnight. The solids were removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate concentrated to dryness to afford crude 5-methyl-1-(tetrahydro-2H-pyran-4-yl)imidazolidin-2-one (190 mg, 47%) which was used without further purification. MS (ESI) m/z: 185.1 (M+H+).

Provenance & Evidence