1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(1-Azidoethyl)-2-methylpyrimidine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 1-(2-methylpyrimidin-5-yl)ethanol (2.48 g, 17 mmol) and diphenylphosphonic azide (9.3 mL, 41 mmol) in toluene (54.5 mL) at 0° C. was added neat 1,8-diazabicyclo[5.4.0]undec-7-ene (6.2 mL, 41 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and then stirred at room temperature overnight. The mixture was diluted with EtOAc (100 mL) and washed with water (100 mL×2). The orangic layer was concentrated in vacuo and purified by silica gel chromatography (0-100% EtOAc/hexane) to afford a colorless oil.

Provenance & Evidence