3-(1-Benzylpiperidin-4-yl)-8-fluoroquinazoline-2,4(1H,3H)-dione → 8-Fluoro-3-(piperidin-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 2250280Notes

Reaction equation

HRID 2250280 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:23](=[O:24])[C:22]3[C:17](=[C:18]([F:25])[CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:26])[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].CO>[F:25][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[NH:16][C:15](=[O:26])[N:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:23]2=[O:24]

Participants

4

Reactant 1

HCID 211021553-(1-Benzylpiperidin-4-yl)-8-fluoroquinazoline-2,4(1H,3H)-dione

Product 1

HCID 211022188-Fluoro-3-(piperidin-4-yl)quinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask containing a solution of 3-(1-benzylpiperidin-4-yl)-8-fluoroquinazoline-2,4(1H,3H)-dione (75.0 mg, 0.21 mmol) and palladium on charcoal (8.00 mg, 0.035 equiv) in methanol (3.00 mL) was flushed first with nitrogen, then hydrogen. The reaction was stirred under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated to give 53 mg (95%) as a white solid which was used without purification. Mass spec.: 264.25 (MH)+.

Workup

  1. customwas flushed first with nitrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customto give 53 mg (95%) as a white solid which
  6. customwas used without purification

Sources & evidence

ORD record
ord-67a6d6a8b2f648efa2923afa4eec7570
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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