Sodium periodate → HCID 12088009, compound

HRID 1169277Notes

Reaction equation

HRID 1169277 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH:18]=CN(C)C)[N:12]([C:23]1[C:24]([CH3:29])=[N:25][CH:26]=[CH:27][CH:28]=1)[C:11]2=[O:30]>O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH:18]=[O:2])[N:12]([C:23]1[C:24]([CH3:29])=[N:25][CH:26]=[CH:27][CH:28]=1)[C:11]2=[O:30]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 540730136-Fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-3-(2-methyl-pyridin-3-yl)-quinazolin-4-one

Product 1

HCID 12088009HCID 12088009, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a well stirred mixture of sodium periodate (1.76 g, 8.26 mmol) in pH 7 buffer (10 mL) and tetrahydrofuran (15 mL) was added 6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-3-(2-methyl-pyridin-3-yl)-quinazolin-4-one (0.69 g, 2.12 mmol) all at once. The mixture warmed slightly to the touch and was stirred for 1 hour at ambient temperature. The reaction was concentrated at reduced pressure and the residue treated with a 1:2 mixture of water and chloroform. The tan solid was collected, washed well with water and chloroform and dried under a stream of nitrogen to afford 0.50 g (80%) of 6-fluoro-3,4-dihydro-3-(2-methyl-pyridin-3-yl)-quinazolin-4-one-2-carboxaldehyde as a 1:1 mixture of free aldehyde and hydrate which had: mp 175-177° C.; 1H NMR δ 9.46 (s, 0.5H) [CHO], 8.53 (br s, 1H), 8.10-8.07 (s, 0.5H), 7.94-7.70 (m, 3.5H), 7.39-7.32 (m, 1H), 6.59 (br s, 0.5H) [hydrate OH], 6.47 (br s, 0.5H) [hydrate OH], 5.17 (s, 0.5H) [hydrate methine CH], 2.20 (s, 3H); APCI MS m/z=284.1 (P+1).

Workup

  1. temperatureThe mixture warmed slightly to the touch
  2. stirringwas stirred for 1 hour at ambient temperature
  3. concentrationThe reaction was concentrated at reduced pressure
  4. additionthe residue treated with a 1:2 mixture of water and chloroform
  5. customThe tan solid was collected
  6. washwashed well with water and chloroform
  7. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-82ab03f4f85545319631f6bdc33591aa
Source dataset
uspto-grants-2003_09
Patent number
US06627755B1

Reaction notes

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