4-Methylbenzaldehyde → [3-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-3-(4-methyl-benzylamino)-propyl]-carbamic acid tert-butyl ester

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Reaction Steps

Formula 107 where R1, R2, R4, R6, R7, R8 and R9 are H: R3 is Chloro; R5 is Benzyl; and R10 is p-Methyl-benzyl: To a solution of [3-amino-3-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-propyl]-carbamic acid tert-butyl ester (700 mg, 1.58 mmol) and DIEA (275 μL, 2.37 mmol) in 50 mL of DCM was added p-tolualdehyde (188 μL, 1.58 mmol). The mixture was stirred for 1 hour, after which sodium triacetoxyborohydride (500 mg, 2.37 mmol) was added. After stirring an additional 3 hours, the mixture was washed with saturated sodium bicarbonate solution, dried over sodium sulfate. The solvents were evaporated to dryness and the residue was purified by flash silica gel chromatography (stepwise gradient 1:4, 1:2, 1:1, 2:1, 4:1 with ethyl acetate:hexanes as eluent) to give the corresponding, pure compound of Formula 107, [3-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-3-(4-methyl-benzylamino)-propyl]-carbamic acid tert-butyl ester (760 mg, 88%).

Provenance & Evidence