Ethanol → HCID 86692252, compound

HRID 1469764Notes

Reaction equation

HRID 1469764 reaction equation
[H-].[Na+].[CH3:3][CH2:4][OH:5].Cl[C:7]1[C:16]2[C:11](=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][N:8]=1>C1COCC1>[CH2:4]([O:5][C:7]1[C:16]2[C:11](=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][N:8]=1)[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 114584714-Chloro-8-nitroquinazoline

Product 1

HCID 86692252HCID 86692252, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-nitroquinazolin-4(3H)-one (Intermediate-7, step-1, 300 mg, 1.57 mmol) in POCl3 (3 mL) was heated at reflux for 2 h. Then the reaction mixture was concentrated and dried to afford 4-chloro-8-nitroquinazoline which was used for the next step without further purification. Then NaH (263 mg, 11.54 mmol, 95%) was added to EtOH (2 mL) at 0° C. and stirred at that temperature for 15 minutes before it was added to a solution of 4-chloro-8-nitroquinazoline in THF (2 mL) at 0° C. Then the reaction mixture was stirred at rt for 4 h. Then the reaction mixture was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 200 mg of the title product. MS (m/z): 220.23 (M+H)+.

Workup

  1. customwas used for the next step without further purification
  2. stirringThen the reaction mixture was stirred at rt for 4 h
  3. customThen the reaction mixture was quenched with water
  4. extractionwas extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. customseparated
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6b3da1defb004981a654868478893aec
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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