Sodium Hydroxide → HCID 10254245, compound

Participants

Reaction Conditions

Reaction Steps

Formula I where R1, R2, R4, R6, R7, R8 and R9 are H, R3 is Chloro; R5 is Benzyl; R10 is p-Methyl-benzyl; and V is N—R′″ where R′″ is H: 3-(4-Methyl-benzyl)-2-oxo-hexahydro-pyrimidine-4-carboxylic acid (2-benzylcarbamoyl-5-chloro-phenyl)-amide (350 mg, 0.713 mmol) was dissolved in 60 mL of ethylene glycol to which was added sodium hydroxide (60 mg, 1.5 mmol). The mixture was stirred at 140° C. for 20 hours and monitored by LC-MS. Following consumption of starting material, the reaction mixture was poured into 100 mL of water. After extraction with DCM, the crude product 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 desired product of Formula I, 3-benzyl-7-chloro-2-[3-(4-methyl-benzyl)-2-oxo-hexahydro-pyrimidin-4-yl]-3H-quinazolin-4-one (180 mg, 53%).

Provenance & Evidence