Acetic Anhydride → 4-Acetylamino-2-allylamino-6-nitroquinazoline

HRID 1250592Notes

Reaction equation

HRID 1250592 reaction equation
[CH2:1]([NH:4][C:5]1[N:14]=[C:13]([NH2:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=2)[N:6]=1)[CH:2]=[CH2:3].[C:19](OC(=O)C)(=[O:21])[CH3:20].C([O-])(=O)C.[Na+].[OH-].[Na+]>C1COCC1>[C:19]([NH:15][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=2)[N:6]=[C:5]([NH:4][CH2:1][CH:2]=[CH2:3])[N:14]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 183264362-Allylamino-4-amino-6-nitroquinazoline

Product 1

HCID 183263884-Acetylamino-2-allylamino-6-nitroquinazolineYield 42.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 mg (1.22 mmol) of 2-allylamino-4-amino-6-nitroquinazoline was dissolved in 5 ml of THF, and then 5.0 g (29.38 mmol) of acetic anhydride and 30 mg (0.37 mmol) of sodium acetate were added thereto, followed by stirring at room temperature for 12 hours. The reaction solution was neutralized with a 1 N aqueous sodium hydroxide solution. Crystals thus precipitated were filtered, followed by washing with water and drying to give 150 mg (42.7%) of the title compound.

Workup

  1. customCrystals thus precipitated
  2. filtrationwere filtered
  3. washby washing with water
  4. customdrying

Sources & evidence

ORD record
ord-61697d17430546e08f2afd113703fad8
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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