Water → 4-Chloro-6-methoxy-7-methylquinazoline

HRID 228890Notes

Reaction equation

HRID 228890 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][CH:8]=[N:7][C:6]2=O.P(Cl)(Cl)([Cl:17])=O.O.C(=O)([O-])O.[Na+]>C(N(CC)C(C)C)(C)C>[Cl:17][C:6]1[C:5]2[C:10](=[CH:11][C:12]([CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178486775HCID 178486775, compound

Product 1

HCID 230783654-Chloro-6-methoxy-7-methylquinazolineYield 66%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
100 °C

Procedure

6-Methoxy-7-methyl-1H-quinazolin-4-one (275 mg) was suspended in N,N-diisopropylethylamine (3.78 ml), phosphorus oxychloride (0.3 ml) was added to the suspension, and the mixture was stirred at 100° C. for 6 hr. The reaction solution was added in small portions to water of 0° C., an aqueous sodium hydrogencarbonate solution was further added thereto, and the mixture was extracted with chloroform. The chloroform layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give 4-chloro-6-methoxy-7-methyl-quinazoline (199 mg, yield 66%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe chloroform layer was then washed with saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-2f935e4814e24ac1961e7d67498bd28b
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…