Water → 2-Acetylamino-4-allylamino-6-nitroquinazoline

HRID 1250595Notes

Reaction equation

HRID 1250595 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH2:18])[N:6]=1)[CH:2]=[CH2:3].[C:19](OC(=O)C)(=[O:21])[CH3:20].C(N(CC)CC)C.O>C(#N)C>[C:19]([NH:18][C:7]1[N:6]=[C:5]([NH:4][CH2:1][CH:2]=[CH2:3])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 183264494-Allylamino-2-amino-6-nitroquinazoline

Product 1

HCID 183264972-Acetylamino-4-allylamino-6-nitroquinazolineYield 80.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After 100 mg (0.41 mmol) of 4-allylamino-2-amino-6-nitroquinazoline was dissolved in 10 ml of acetonitrile, 84 mg (0.82 mmol) of acetic anhydride and 0.06 ml (0.45 mmol) of triethylamine were added thereto, and then the reaction mixture was subjected to heating under reflux overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate, washing successively with a saturated aqueous sodium hydrogen carbonate solution and brine and drying over anhydrous sodium sulfate. The solvent was distilled off, followed by recrystallization from ethyl acetate-hexane to give 95 mg (80.7%) of the title compound.

Workup

  1. temperatureto heating
  2. temperatureunder reflux overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashing successively with a saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdrying over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customfollowed by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7e07d75a983747129548e60364d33475
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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