Water → HCID 18326572, compound

HRID 1250585Notes

Reaction equation

HRID 1250585 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]([NH2:24])/[CH:21]=[CH:22]/[CH3:23].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:24][CH2:20]/[CH:21]=[CH:22]/[CH3:23])[N:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12602976209907-25-5HCID 183264874-Allylamino-2-chloro-6-nitroquinazoline

Product 1

HCID 18326572HCID 18326572, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

150 mg (0.57 mmol) of 4-allylamino-2-chloro-6-nitroquinazoline was dissolved in 2 ml of acetonitrile, and 305 mg (2.83 mmol) of trans-2-butenylamine hydrochloride and 0.39 ml (2.83 mmol) of triethylamine were added thereto, followed by stirring at 50° C. for 6 hours. To the reaction solution was water added, 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 138 mg (yield: 80.9%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-2209ba33f2764431a12fe9c21fc2b7f4
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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