Acetoacetic Acid → HCID 135763125, compound

HRID 1372997Notes

Reaction equation

HRID 1372997 reaction equation
[OH:1][CH: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.[CH3:25][C:26](CC(O)=O)=[O:27].[OH-].[Na+]>C(OC(=O)C)(=O)C>[C:26]([O:1][CH: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:27])[CH3:25]

Participants

6

Reactant 4

HCID 96Acetoacetic AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 135763119HCID 135763119, compound

Product 1

HCID 135763125HCID 135763125, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

7-(2-Hydroxy-3-(pyrrolidin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (5 g) was suspended in acetic anhydride (7.4 ml). The reaction mixture was stirred at ambient temperature for 90 minutes followed by addition of water (2.8 ml) and the reaction mixture was stirred an additional 2 hours in order to hydrolyse the diacetate byproduct. The mixture was cooled with an ice bath, more water (100 ml) was added and a solution of sodium hydroxide (2N) was slowly added to adjust the pH to 9.5. The product was extracted with dichloromethane (3 times) the organic phases were combined, washed with water, brine, dried over magnesium sulphate, filtered and the solvent evaporated to give 7-(2-acetoxy-3-(pyrrolidin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (4.2 g) as a white solid.

Workup

  1. stirringthe reaction mixture was stirred an additional 2 hours in order
  2. temperatureThe mixture was cooled with an ice bath
  3. extractionThe product was extracted with dichloromethane (3 times) the organic phases
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-6144764b299543d99f9c01e7d3ae7192
Source dataset
uspto-grants-2007_01
Patent number
US07160889B2

Reaction notes

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