Methyl iodide → HCID 22663137, compound

HRID 275739Notes

Reaction equation

HRID 275739 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[C:18]([NH:30][CH3:31])[N:17]=2)[CH:13]=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:32]([N-]C(C)C)(C)C.[Li+].CI.C(OCC)(=O)C>O1CCCC1.CCCCCC>[C:1]([N:9]([C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[C:18]([NH:30][CH3:31])[N:17]=2)[CH:13]=[CH:14][CH:15]=1)[CH3:32])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 2724682Lithium diisopropylamideHCID 9844682HCID 9844682, compound

Product 1

HCID 22663137HCID 22663137, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

207 mg of 4-(3-benzoylaminophenyl)-6,7-dimethoxy-2-methylaminoquinazoline obtained in Example 1 was dissolved in 5 ml tetrahydrofuran, and 0.667 ml of 1.5 M lithium diisopropylamide in hexane was added dropwise thereto at −70° C. After the dropwise addition, the mixture was stirred at −70° C. for 30 minutes, and then 284 mg of methyl iodide was added thereto. The mixture was returned to room temperature and further stirred for 1 hour. After ethyl acetate was added thereto, the mixture was washed with water twice and with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (hexane:ethyl acetate=1:3) The product was recrystallized from hexane-ethyl acetate to give 75 mg of the title compound as pale yellow crystals.

Workup

  1. customat −70° C
  2. additionAfter the dropwise addition
  3. customwas returned to room temperature
  4. stirringfurther stirred for 1 hour
  5. washthe mixture was washed with water twice
  6. dry with materialwith brine, and then dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe crude product was purified
  9. customseparated by silica gel column chromatography (hexane:ethyl acetate=1:3) The product
  10. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-f5871e0e290a49d6a7cbcf689d56ba25
Source dataset
uspto-grants-2002_03
Patent number
US06352989B1

Reaction notes

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