Dimethylformamide dimethyl acetal → HCID 54073013, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[C:5]2=[O:20].CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[CH:23][N:24]([CH3:26])[CH3:25])[N:6]([C:13]1[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[C:5]2=[O:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
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).
Workup
- temperaturethe reaction was heated at 140° C. for 16 hours
- temperatureThe reaction was cooled to ambient temperature
- concentrationconcentrated at reduced pressure
- customThe dark residue was triturated with ether
- customthe dark purple crystalline solid which formed
- customwas collected
- customdried
Sources & evidence
- ORD record
- ord-8eeb4d973a084245ac2d82300ec5ea2b
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921764B2
Reaction notes
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