Water → HCID 18326490, compound

HRID 1250588Notes

Reaction equation

HRID 1250588 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](Cl)[N:6]=1)[CH:2]=[CH2:3].Cl.[CH2:20]([O:23][CH2:24][CH2:25][NH2:26])[CH2:21][CH3:22].C(N(CC)CC)C.O>C(#N)C>[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:26][CH2:25][CH2:24][O:23][CH2:20][CH2:21][CH3:22])[N:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 18326446221043-83-0HCID 183264874-Allylamino-2-chloro-6-nitroquinazoline

Product 1

HCID 18326490HCID 18326490, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

100 mg (0.38 mmol) of 4-allylamino-2-chloro-6-nitroquinazoline was dissolved in 1.5 ml of acetonitrile, and 124 mg (0.76 mmol) of 2-propoxyethylamine hydrochloride and 196 mg (1.94 mmol) of triethylamine were added thereto, followed by stirring at 80° C. for 15 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate, washing brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 91 mg (72.3%) of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing 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-4b9c537907a7487f9c86049134ad632a
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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