Dimethylformamide dimethyl acetal → HCID 54073013, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-fluoro-3,4-dihydro-2-methyl-3-(2-methyl-pyridin-3-yl)-quinazolin-4-one (1.02 g, 3.79 mmol) and dimethylformamide dimethyl acetal (1.01 mL, 7.58 mmol) in dimethylformamide (5 mL) was heated to 140° C. for 24 hours. Additional dimethylformamide dimethyl acetal (2 mL) was added and the reaction was heated at 140° C. for 16 hours. The reaction was cooled to ambient temperature and concentrated at reduced pressure. The dark residue was triturated with ether and the dark purple crystalline solid which formed was collected and dried to give 0.69 g (56%) of 6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-3-(2-methyl-pyridin-3-yl)-quinazolin-4-one which had: 1H NMR δ 8.61 (dd, J=1.5, 5 Hz, 1 H), 7.87 (d, J=12.3 Hz, 1 H), 7.78 (dd, J=3, 8.5 Hz, 1 H), 7.50-7.45 (m, 2 H), 7.39-7.29 (m, 2 H), 3.97 (d, J=12.3 Hz, 1 H), 2.86 (br s, 6 H), 2.35 (s, 3 H).

Provenance & Evidence