Sodium hydride → HCID 86757267, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(diphenylmethylene)glycine t-butyl ester (1.30 g, 4.40 mmol) in 10 mL of DMF is treated with sodium hydride (60% in mineral oil, 0.250 g, 6.25 mmol) at 25° C. to give a red orange solution. After 1 h, the temperature is raised to 60° C. and a solution of the title B compound, 3-(4-iodobutyl)-1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinazoline (1.58 g, 4.41 mmol) in 10 mL of DMF is added dropwise over 10 min. After stirring for 5 h at 60 ° C. and 58 h at 25° C. the solvent is evaporated under reduced pressure, and the residue is partioned between 75 mL of ethyl acetate and 25 mL of water. The organic solution is washed with three 25 mL portions of brine, dried over anhydrous MgSO4, and concentrated to give 2.15 g of 2-(benzhydrylideneamino)-6-(1,2,3,4-tetrahydro-1-methyl-2,4-dioxoquinazolin-3-yl)hexanoic acid t-butyl ester as a yellow oil.

Provenance & Evidence