Sodium hydride → HCID 18326551, compound

HRID 1250590Notes

Reaction equation

HRID 1250590 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].[H-].[Na+].[C:21]([N:25]=[C:26]=[O:27])([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[CH2:1]([NH:4][C:5]1[N:14]=[C:13]([NH:15][C:26](=[O:27])[NH:25][C:21]([CH3:24])([CH3:23])[CH3:22])[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]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62412tert-Butyl isocyanateHCID 183264362-Allylamino-4-amino-6-nitroquinazoline

Product 1

HCID 18326551HCID 18326551, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5 ml of a solution of 165 mg (0.67 mmol) of 2-allylamino-4-amino-6-nitroquinazoline in THF was added 17 mg (10.7 mmol) of sodium hydride. After the mixture was stirred under ice cooling for 0.5 hour, 76 mg (0.77 mmol) of t-butylisocyanate was added, followed by stirring for 1.5 hours at room temperature. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with chloroform (10 ml×3). After the organic layer was washed with brine and then dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by a silica gel chromatography to give 79 mg (yield: 34.2%) of the title compound.

Workup

  1. stirringby stirring for 1.5 hours at room temperature
  2. additionwas added to the reaction mixture
  3. extractionfollowed by extraction with chloroform (10 ml×3)
  4. washAfter the organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-cafad65260574bd39bed4c56c838b4e7
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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