Magnesium Bromide → 5-hydroxy-7-methoxyquinazolin-4(3H)-one

HRID 1917792Notes

Reaction equation

HRID 1917792 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[NH:6][CH:7]=[N:8]2.[Mg+2].[Br-].[Br-]>N1C=CC=CC=1>[OH:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[NH:6][CH:7]=[N:8]2

Participants

4

Reactant 2

HCID 82241Magnesium BromideHCID 1355106675,7-dimethoxyquinazolin-4(3H)-one

Product 1

HCID 1355106955-hydroxy-7-methoxyquinazolin-4(3H)-oneYield 98.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 5,7-dimethoxyquinazolin-4(3H)-one (4.80 g, 23.3 mmol) in pyridine (50 mL) at room temperature was slowly added MgBr2 (4.29 g, 23.3 mmol). It was heated to reflux for 1.5 hour. After solvent was evaporated under reduced pressure, to the residue was added a solution of AcOH (10 mL) in water (50 mL). A solid was precipitated. It was filtered, washed with water, and dried under vacuum with P2O5 to afford 5-hydroxy-7-methoxyquinazolin-4(3H)-one as solid (4.398 g, 98%). 1H NMR (300 MHz, DMSO-d6) δ 11.95 (br, 1H), 8.08 (s, 1H), 6.63 (s, 1H), 6.50 (s, 1H), 3.85 (s, 3H); LC-MS (ESI) m/z 193 (M+H)+.

Workup

  1. temperatureIt was heated
  2. temperatureto reflux for 1.5 hour
  3. customAfter solvent was evaporated under reduced pressure, to the residue
  4. additionwas added a solution of AcOH (10 mL) in water (50 mL)
  5. customA solid was precipitated
  6. filtrationIt was filtered
  7. washwashed with water
  8. dry with materialdried under vacuum with P2O5

Sources & evidence

ORD record
ord-9a91ae0fd7714dc684e84fc29bf2779c
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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