Water → HCID 18326561, compound

HRID 1250593Notes

Reaction equation

HRID 1250593 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+].[CH3:21][CH:22]([CH3:28])[CH2:23][O:24][C:25](Cl)=[O:26].O>CN(C=O)C>[CH2:1]([NH:4][C:5]1[N:14]=[C:13]([NH:15][C:25]([O:24][CH2:23][CH:22]([CH3:28])[CH3:21])=[O:26])[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

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 62365Isobutyl chloroformateHCID 183264362-Allylamino-4-amino-6-nitroquinazoline

Product 1

HCID 18326561HCID 18326561, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (2.04 mmol) of 2-allylamino-4-amino-6-nitroquinazoline was dissolved in 5 ml of DMF, and then 80 mg (2.33 mmol) of 70% sodium hydride and 280 mg (2.05 mmol) of 2-methylpropoxycarbonyl chloride were added thereto under ice cooling, followed by stirring for 3 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate, successive 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 131 mg (19.1%) of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washsuccessive washing with brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-383bd897c61645428e45cec43e6910ba
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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