Water → HCID 136067009, compound

HRID 454253Notes

Reaction equation

HRID 454253 reaction equation
[OH:1][C@H:2]([CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[NH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:16][CH3:17].[C:24](OC(=O)C)(=[O:26])[CH3:25].O>>[C:24]([O:1][C@H:2]([CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[NH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:16][CH3:17])(=[O:26])[CH3:25]

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 136087581HCID 136087581, compound

Product 1

HCID 136067009HCID 136067009, compoundYield 65.6%

Procedure

A mixture of (2R)-7-(2-hydroxy-3-(pyrrolidin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (803 mg, 2.51 mmol) in acetic anhydride (1.2 ml, 12.5 mmol) was stirred at ambient temperature for 1 hour. Water (360 μl, 20 mmol) was added and stirring was continued for 90 minutes. The mixture was partitioned between aqueous sodium hydrogen carbonate and methylene chloride. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated. The residue was triturated with ether, filtered and dried under vacuum to give (2R)-7-(2-acetoxy-3-(pyrrolidin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (595 mg, 65%).

Workup

  1. stirringstirring
  2. waitwas continued for 90 minutes
  3. customThe mixture was partitioned between aqueous sodium hydrogen carbonate and methylene chloride
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was triturated with ether
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-b37412c518c7420b8d2c6978f1f56ee9
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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