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 2270294Notes

Reaction equation

HRID 2270294 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 dietbyl 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 dietbyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-8c4fbcdf28c8463d97333378e07f9d89
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

Loading…