Sodium hydride → HCID 67013703, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[3-(4-chloro-phenyl)-allyl]-piperazine-2,3-dione (60 mg, 0.23 mmol) in 1.5 mL of DMF is added NaH (10 mg of a 60% dispersion in mineral oil, 0.24 mmol). The mixture is heated at 55° C. for 20 min. To the solution is added 4-amino-7-chloromethyl-quinazoline (49 mg, 0.25 mmol), and the resulting mixture is heated at 55° C. for 20 min as a white precipitate is formed. After this time, reaction mixture is quenched with a few drops of H2O and MeOH, then concentrated. The crude product is purified by RP-HPLC, eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 70% CH3CN/H2O (0.1% TFA) over 30 minutes, and the appropriate product fractions are combined and lyopholized to provide the title compound (56 mg, 0.10 mmol) as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 9.78 (bs, 2H), 8.83 (s, 1H), 8.40 (s, 1H), 7.72 (d, 1H), 7.65 (s, 1H), 7.49 (d, 2H), 7.38 (d, 2H), 6.61 (d, 1H), 6.30 (dt, 1H), 4.80 (s, 2H), 4.18 (d, 2H), 3.59 (m, 4H). ISP MS, [M+H]+=422.

Provenance & Evidence