Hydrogen Peroxide → HCID 178491893, compound

HRID 1710823Notes

Reaction equation

HRID 1710823 reaction equation
I.[Cl:2][C:3]1[C:4]([CH3:18])=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[N:9]=[C:8](SC)[NH:7][CH:6]2[CH3:17].[OH-].[NH4+:20].[OH-].[Na+].OO>C(#N)C.O>[Cl:2][C:3]1[C:4]([CH3:18])=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[N:9]=[C:8]([NH2:20])[NH:7][CH:6]2[CH3:17]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 178491895HCID 178491895, compound

Product 1

HCID 178491893HCID 178491893, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
170 °C

Procedure

6-Chloro-8-methoxy-4,5-dimethyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (119 mg, 0.30 mmol) was suspended in a mixture of ammonium hydroxide (0.22 ml, 25% in H2O, 3 mmol) and acetonitrile (0.9 ml), and heated in a microwave oven to 170° C. (30 min). The reaction was cooled in an ice bath and treated with 1N aqueous sodium hydroxide solution (0.9 ml) and 5-6 drops of concentrated solution of aqueous hydrogen peroxide. A little water was added, and the crude product precipitated and was filtered off. It was purified by column chromatography (silica gel, ethyl acetate/acetone/acetic acid=12/4/1) and was set neutral with 1N aqueous sodium hydroxide solution to yield after drying the title compound as a light grey solid (45 mg, 63%).

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customthe crude product precipitated
  3. filtrationwas filtered off
  4. customIt was purified by column chromatography (silica gel, ethyl acetate/acetone/acetic acid=12/4/1)
  5. customto yield
  6. dry with materialafter drying the title compound as a light grey solid (45 mg, 63%)

Sources & evidence

ORD record
ord-7b9a9b20fc644e839ae7da318c6fecd8
Source dataset
uspto-grants-2010_09
Patent number
US07790733B2

Reaction notes

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