Allylamine → HCID 20718746, compound

HRID 1250555Notes

Reaction equation

HRID 1250555 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[N:8]=[C:7](Cl)[N:6]=1)[CH:2]=[CH2:3].[CH2:17]([NH2:20])[CH:18]=[CH2:19].C(=O)([O-])O.[Na+]>CN1CCN(C)C1=O>[CH2:17]([NH:20][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]([Cl:15])[CH:13]=2)[N:8]=1)[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 18326409HCID 18326409, compound

Product 1

HCID 20718746HCID 20718746, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
100 °C

Procedure

In 1 ml of 1,3-dimethyl-2-imidazolidinone was dissolved 300 mg (1.18 mmol) of 4-allylamino-2,6-dichloroquinazoline, and after 110 mg (1.87 mmol) of allylamine was added to the resulting solution, the mixture was stirred in a sealed tube at 100° C. for 10 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, 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 283 mg (yield: 87.3%) of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing 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-19c8078072294aefb6e7ed229f5c5572
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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