HCID 87619359, compound → HCID 87619004, compound

Participants

Reaction Steps

To a solution of 1.06 g (0.0031 mole) of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-(3-methyl-butyl)-amino]-2-methyl-propionic acid ethyl ester (IV-27) in 20 mL of acetic acid, was added 1.0 g (0.0179 g-atom) of iron powder. The mixture was heated at 80 degrees for 2 hours and then filtered through Celite while still hot. The filtercake was washed with 100 mL of ethyl acetate (100 mL), and the combined filtrate washed successively with 100 mL of water 100 mL of 7.4 M ammonium hydroxide, 100 mL of water and 100 mL of brine. The aqueous layers were extracted with 100 mL of ethyl acetate, and the combined ethyl acetate layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate—dichloromethane (1:1) to give 0.61 g of (rac)-2-chloro-7-methyl-9-(3-methyl-butyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-27) as white crystalline solid.

Provenance & Evidence