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 1177801Notes

Reaction equation

HRID 1177801 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-5a2ddbe9f9014b56b1f989598aea418d
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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