Sodium hydride → HCID 19023220, compound

Participants

Reaction Steps

A mixture of 7-fluoro-6-methoxycarbonylamino-4-propargyl-2H-1,4-benzoxazin-3(4H)-one (1.4 g) and ethyl 3-amino-4,4,4-trifluorocrotonate was dissolved in dimethylformamide (5 g), and sodium hydride (0.2 g) was added thereto. The resultant mixture was stirred for 30 minutes while cooling with ice and heated under reflux for 3 hours. After cooling, 2,4-dinitrophenoxyamine (1.2 g) was added thereto, and the resultant mixture was stirred at 40° C. for 3 hours. After completion of the reaction, the reaction mixture was combined with water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3-amino-1-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6yl]-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione (0.2 g).

Provenance & Evidence