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Methyl iodide → HCID 22663137, compound

HRID 392174
Notes
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Reaction equation

HRID 392174 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 8028Tetrahydrofuran
Solvent
HCID 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)
  10. customThe product was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-c3a8e35d269b493ba369880e5c0a4ff1
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800644B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes