3-Benzyloxy-1-ethyl-5,6,8-trifluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione → 1-Ethyl-5,6,8-trifluoro-3-hydroxy-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione

HRID 2416903Notes

Reaction equation

HRID 2416903 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([F:27])[C:14]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[C:15]([F:21])[C:16]=2[F:20])[N:11]([CH2:28][CH3:29])[C:10]1=[O:30])C1C=CC=CC=1.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[B+3]>FC(F)(F)C(O)=O>[CH2:28]([N:11]1[C:12]2[C:17](=[C:16]([F:20])[C:15]([F:21])=[C:14]([N:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[C:13]=2[F:27])[C:18](=[O:19])[N:9]([OH:8])[C:10]1=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 226329973-Benzyloxy-1-ethyl-5,6,8-trifluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dioneHCID 178525683HCID 178525683, compound

Product 1

HCID 226329941-Ethyl-5,6,8-trifluoro-3-hydroxy-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dioneYield 92.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of 3-benzyloxy-1-ethyl-5,6,8-trifluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione (Example X-3, 0.15 g, 0.36 mmol) in trifluoroacetic acid (5.0 mL) was reacted with a 1.0 M solution of boron tris(trifluoroacetate) (1.8 mL, 1.8 mmol) in TFA and allowed to stir for 1 hour. The mixture was then concentrated and the residue dissolved in methanol and concentrated. This process was repeated three times. The residue was then triturated from diethyl ether and filtered to provide 0.11 g of the title compound as a solid, mp 223-225° C.

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutionthe residue dissolved in methanol
  3. concentrationconcentrated
  4. customThe residue was then triturated from diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-cb99553ab4fe461faf2dbc042f93cead
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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