Sodium hydride → 3-(3,4-dimethyl-benzoyl)-1-pyrimidin-2-ylmethyl-1H-quinolin-4-one

Participants

Reaction Conditions

Reaction Steps

Compound 4k was prepared following the procedure outlined in Step 3 of Example 1. Briefly described here, 97 mg (0.35 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one, 18 mg (0.45 mmol) of 60% sodium hydride and 66 mg (0.51 mmol) of 2-chloromethyl pyrimidine (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351) were combined in 1 mL N,N-dimethylformamide and heated at 80° C. for 2 h. The product was purified using reverse phase HPLC (mobile phase with a gradient 10-50% acetonitrile in 50 min), to give 57 mg of a pale yellow solid 4k as trifluoroacetate salt: LC-MSD, m/z for C23H19N3O2 [M+H]+=370.5, HPLC retention time: 2.4 min; 1H NMR (400 MHz, CDCl3): δ 2.3 (s, 3H), 2.35 (s, 3H), 5.6 (s, 2H), 7.15-7.2 (m, 1H), 7.25-7.3 (m, 1H), 7.4-7.5 (m, 1H), 7.5-7.55 (m, 1H), 7.6-7.7 (m, 3H), 8.4-8.5 (m, 2H), 8.7-8.75 (m, 2H).

Provenance & Evidence