Water → 4-Allylamino-6-nitro-2-(propylcarbamoyl)aminoquinazoline

HRID 1250596Notes

Reaction equation

HRID 1250596 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].[CH2:19]([N:22]=[C:23]=[O:24])[CH2:20][CH3:21].C(N(CC)CC)C.O>C1COCC1>[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]([NH:18][C:23](=[O:24])[NH:22][CH2:19][CH2:20][CH3:21])[N:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 183264494-Allylamino-2-amino-6-nitroquinazoline

Product 1

HCID 183264484-Allylamino-6-nitro-2-(propylcarbamoyl)aminoquinazolineYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After 200 mg (0.82 mmol) of 4-allylamino-2-amino-6-nitroquinazoline was dissolved in 10 ml of THF, 153 mg (1.80 mmol) of propylisocyanate and 0.13 ml (0.90 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 with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 218 mg (80.5%) of the title compound.

Workup

  1. temperatureto heating
  2. temperatureunder reflux overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashing with brine
  5. dry with materialdrying over anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-1b2d28acb524461e8e251cfc2ddcc283
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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