Ammonium formate → 6-Methoxy-7-hydroxyquinazolin-4-one

HRID 1668670Notes

Reaction equation

HRID 1668670 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[NH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CN(C)C=O>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[NH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 1356099526-Methoxy-7-hydroxyquinazolin-4-oneYield 60.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

10% Palladium on carbon (8.3 g) was added to a suspension of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (50 g, 0.177 mol) in dimethylformamide (800 ml) under nitrogen. Ammonium formate (111.8 g, 1.77 mol) was then added in portions over 5 minutes. The reaction mixture was stirred for one hour at ambient temperature then heated to 80° C. for a further hour. The reaction mixture was filtered hot through diatomaceous earth and the residues washed with dimethylformamide. The filtrate was then concentrated and the residue suspended in water. The pH was adjusted to 7.0 using 2M sodium hydroxide and the resulting mixture was stirred at ambient temperature for one hour. The solid was filtered, washed with water and dried over phosphorus pentoxide yielding 7-hydroxy-6-methoxy-3,4-dihydroquinazolin-4-one as a white solid (20.52 g, 60%).

Workup

  1. temperaturethen heated to 80° C. for a further hour
  2. filtrationThe reaction mixture was filtered hot through diatomaceous earth
  3. washthe residues washed with dimethylformamide
  4. concentrationThe filtrate was then concentrated
  5. stirringthe resulting mixture was stirred at ambient temperature for one hour
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-e42494efaa6b416bb4575cfdf5a398f4
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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