1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 90426706, compound

Participants

Reaction Conditions

Reaction Steps

A solution of prop-1-en-2-yl(tetrahydro-2H-pyran-4-yl)carbamate (0.50 g, 2.70 mmol) in dioxane (20 mL) was treated with DBU (0.1 mL) and propargylamine (0.149 g, 2.70 mmol) and heated at 90° C. overnight. The mixture was cooled to RT, treated with brine and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, concentrated to dryness, treated with Et2O and the resulting solid collected via filtration to afford 1-(prop-2-yn-1-yl)-3-(tetrahydro-2H-pyran-4-yl)urea (400 mg, 81%). 1H NMR (400 MHz, DMSO-d6): δ 6.00 (m, 1 H), 5.99 (m, 1 H), 3.76 (m, 2 H), 3.75 (m, 2 H), 3.56 (m, 1 H), 3.30 (m, 2 H), 3.02 (t, J=2.5 Hz, 1 H), 1.68 (m, 2 H), 1.29 (m, 2H); MS (ESI) m/z: 183.1 (M+H+).

Provenance & Evidence