Methanol → HCID 58243376, compound

Participants

Reaction Steps

To a stirred solution of 1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-ol (50 mg, 0.197 mmol) in DMSO (2 ml) was added NaH (16 mg of a 60% dispersion in mineral oil, 0.40 mmol) at room temperature in one portion. The suspension was stirred for 2 hours at room temperature then 2-chloro-5-fluoro-pyrimidine (26 mg, 0.20 mmol) was added in one portion. The mixture was heated at 60° C. in a sealed tube for 16 hours. After cooling to room temperature the solution was treated with MeOH (8 μl, 0.20 mmol) and NaH (16 mg, 0.40 mmol, 60 in mineral oil) and heated at 60° C. in a sealed tube for 16 hours. After cooling to room temperature the reaction was diluted with dichloromethane (30 ml) and washed twice with saturated NaHCO3 (15 ml), dried (Na2SO4), filtered and concentrated at reduced pressure. The residue was purified by FCC (DCM/MeOH/NH3 with gradient, 98:2:1 to 90:10:1) to provide the title compound as colourless oil (20 mg, 28%).

Provenance & Evidence