HCID 22632906, compound → HCID 9948030, compound

HRID 2270265Notes

Reaction equation

HRID 2270265 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]([CH2:26][CH3:27])[C:10]1=[O:28])C1C=CC=CC=1.[H][H]>C1COCC1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH2:26]([N:11]1[C:12]2[C:17](=[CH:16][C:15]([F:20])=[C:14]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:13]=2)[C:18](=[O:19])[N:9]([OH:8])[C:10]1=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 22632906HCID 22632906, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9948030HCID 9948030, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Five percent Pd/BaSO4 (60 mg) was added to a solution of 3-benzyloxy-1-ethyl-6-fluoro-7-pyrrolidinyl-1H-quinazoline-2,4-dione (Example E, 0.21 g, 0.55 mmol) in 16 mL of THF. The mixture was shaken under 50 PSI of hydrogen for 31 hours, filtered, and concentrated to afford 0.16 g of a solid. This solid was dissolved in 1N sodium hydroxide and washed with chloroform. The chloroform layer was back extracted with sodium hydroxide, and the combined basic extracts were acidified to pH 3. The aqueous layer was extracted with chloroform, dried over magnesium sulfate, and concentrated to give 0.11 g of the title compound as a solid, mp 170-171° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3e202dcdb95047cd859c351bcd19d46d
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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