Ethanolamine → 8-(Aminomethyl)-10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione

Participants

Reaction Conditions

Reaction Steps

Ethanolamine (108 μl, 1.790 mmol) was added to a solution of 10-(5-chlorofuran-2-yl)-8-((1,3-dioxoisoindolin-2-yl)methyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione (106 mg, 0.179 mmol) in toluene (3087 μl). The mixture was stirred at 70° C. for 6.5 hours then at room temperature for 16 hours. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (50 ml). The organic phase was washed with 1M NaOH(aq) (20 ml) passed through a hydrophobic frit and evaporated under vacuum to afford the title compound as a mixture of diastereomers.

Provenance & Evidence