4-Methylbenzaldehyde → HCID 9889643, compound

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Reaction Steps

Formula I where U—V is —N(R6)—CReRf—; R1, R2, R4, and Ra to Rf are H; R3 is chloro; R5 is benzyl: and R6 is p-methyl-benzyl: Crude 3-benzyl-7-chloro-1-(pyrrolidine-2-carbonyl)-2,3-dihydro-1H-quinazoline-4-one (170 mg, 0.50 mmol) dissolved in dichloromethane (5 mL) was treated with p-tolualdehyde (80 μL, 0.7 mmol) and NaHB(OAc)3 (350 mg, 1.65 mmol), and the mixture was stirred for 40 minutes at room temperature. The reaction was quenched with saturated NaHCO3 (2.2 mL) and the aqueous phase extracted with dichloromethane (25 mL). The organic layers were combined and dried over Na2SO3, filtered and concentrated under vacuum. The crude residue was purified by silica gel chromatography using a stepwise gradient of 20% ethyl acetate/hexanes to 50% methanol/ethyl acetate as eluent to give 52.5 mg (24% yield) of desired product of Formula I, 3-benzyl-7-chloro-2-[1-(4-methyl-benzyl)-pyrrolidin-2-yl]-3Hquinazolin4-one. LRMS (MH+) m/z 445.

Provenance & Evidence