3-Benzyloxy-1-(2,4-difluorophenyl)-6-fluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione → 1-(2,4-Difluorophenyl)-6-fluoro-3-hydroxy-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione

HRID 2416906Notes

Reaction equation

HRID 2416906 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[C:15]([F:20])[CH:16]=2)[N:11]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])[C:10]1=[O:34])C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[F:33][C:27]1[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]=1[N:11]1[C:12]2[C:17](=[CH:16][C:15]([F:20])=[C:14]([N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[CH:13]=2)[C:18](=[O:19])[N:9]([OH:8])[C:10]1=[O:34]

Participants

5

Reactant 2

HCID 226329513-Benzyloxy-1-(2,4-difluorophenyl)-6-fluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 226329611-(2,4-Difluorophenyl)-6-fluoro-3-hydroxy-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dioneYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Twenty percent Pd/C (50 mg) was added to a solution of 3-benzyloxy-1-(2,4-difluorophenyl)-6-fluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione (Example K-4, 0.22 g, 0.5 mmol) in 40 mL of THF, and this was shaken under 50 PSI of hydrogen for 16 hours. The mixture was filtered and concentrated to afford 0.19 g of a solid. This solid was triturated with ether and filtered to give 0.08 g of the title compound as a solid, mp 232-234° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-43b344208b534d789b7ea45333d4a08d
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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