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

HRID 2270291Notes

Reaction equation

HRID 2270291 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]([CH:26]2[CH2:28][CH2:27]2)[C:10]1=[O:29])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>[CH:26]1([N:11]2[C:12]3[C:17](=[CH:16][C:15]([F:20])=[C:14]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH:13]=3)[C:18](=[O:19])[N:9]([OH:8])[C:10]2=[O:29])[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 178999383-Benzyloxy-1-cyclopropyl-6-fluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dioneHCID 178525683HCID 178525683, compound

Product 1

HCID 226329081-Cyclopropyl-6-fluoro-3-hydroxy-7-(pyrrolidin-1-yl)-1H-quinazoline-2,4-dioneYield 62.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of 3-benzyloxy-1-cyclopropyl-6-fluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione (Example F-3, 0.15 g, 0.38 mmol) in trifluoroacetic acid (TFA, 3.0 mL) was reacted with a 1.0 M solution of boron tris(trifluoroacetate) (1.5 mL, 1.5 mmol, Angew. Chem, Internal. Ed., 1973;12:147) in TFA and allowed to stir for 2 hours. The mixture was then concentrated and the residue diluted in methanol and concentrated. This process was repeated two times. The residue was then triturated from diethyl ether/hexanes and filtered to provide 0.073 g of the title compound as solid, mp 248-250° C. (dec.).

Workup

  1. concentrationThe mixture was then concentrated
  2. additionthe residue diluted in methanol
  3. concentrationconcentrated
  4. customThe residue was then triturated from diethyl ether/hexanes
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ba7f0409c0634607b5b6a48f810f90ad
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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