Dimethylformamide dimethyl acetal → HCID 54061431, compound

HRID 1169272Notes

Reaction equation

HRID 1169272 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=3)[N:10]=[C:9]2[CH3:20])=[CH:6][CH:5]=[CH:4][N:3]=1.CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>CN(C)C=O>[Cl:1][C:2]1[C:7]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=3)[N:10]=[C:9]2[CH:20]=[CH:23][N:24]([CH3:26])[CH3:25])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 223474103-(2-chloro-pyridin-3-yl)-6-fluoro-2-methyl-3H-quinazolin-4-one

Product 1

HCID 54061431HCID 54061431, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-chloro-pyridin-3-yl)-6-fluoro-2-methyl-3,4-dihydro-quinazolin-4-one (3.5 g, 12.0 mmol) and dimethylformamide dimethyl acetal (3.2 mL, 24 mmol) in dimethylformamide (12 mL) was refluxed for 24 hours. The reaction was cooled to ambient temperature and concentrated at reduced pressure to afford an orange solid. The solid was triturated with ethanol and the yellow crystalline solid was collected and dried to give 3.61 g (87%) of 3-(2-chloro-pyridin-3-yl)-6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one, which had: mp 197-200° C.; H 1H NMR δ 8.46 (dd, J=1.5, 5 Hz, 1H), 7.85 (d, J=12.2 Hz, 1H), 7.70 (dd, J=3, 8.5 Hz, 1H), 7.68-7.65 (m, 1H), 7.45-7.38 (m, 2H), 7.31 (dt, J=3, 8.5 Hz, 1H), 3.87 (d, J=12.2 Hz, 1H), 2.80 (br s, 6H). Analysis calculated for C17H14ClFN4O: C, 59.22; H, 4.09; N, 16.25. Found: C, 59.14; H, 3.96; N, 16.25.

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationconcentrated at reduced pressure
  3. customto afford an orange solid
  4. customThe solid was triturated with ethanol
  5. customthe yellow crystalline solid was collected
  6. customdried

Sources & evidence

ORD record
ord-5c5b5b24f2d4447d908a78c6982ca05a
Source dataset
uspto-grants-2003_09
Patent number
US06627755B1

Reaction notes

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