Proton sponge → HCID 54583743, compound

Participants

Reaction Steps

1,8-Bis-(dimethylamino)naphthalene (80 mg, 0.37 mmol) was added to a solution of 7-benzyl-2-(3-chlorobenzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine of Preparation 28, Step C, (135 mg, 0.37 mmol) in dichloromethane (5 ml). Then 1-chloroethyl chloroformate (80.9 μl, 0.74 mmol) was added and stirred at room temperature for 16 h. The reaction mixture was diluted with dichloromethane (10 ml) then washed with 5% aqueous citric acid (15 ml). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was dissolved in methanol (5 ml) then heated to reflux, under nitrogen, for 1.5 h. The reaction mixture was concentrated in vacuo then the residue was partitioned between dichloromethane (10 ml) and 1N NaOH (10 ml). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with DCM:MeOH:0.880NH3 (100:0:0 to 90:10:1), to afford the title compound as a yellow oil in 18% yield, 18 mg.

Provenance & Evidence