Sodium Chloride → HCID 21106341, compound

HRID 1765028Notes

Reaction equation

HRID 1765028 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:18]=[C:17]([NH:19]CCO)[C:16]2[C:15]3[CH:23]=[CH:24][N:25]([CH3:26])[C:14]=3[C:13](C3SC=CC=3)=[CH:12][C:11]=2[N:10]=1.[OH-].[Na+].C[I:35].[Cl-].[Na+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>[I:35][C:13]1[C:14]2[N:25]([CH3:26])[CH:24]=[CH:23][C:15]=2[C:16]2[C:11]([CH:12]=1)=[N:10][C:9]([NH2:8])=[N:18][C:17]=2[NH2:19]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 11775359HCID 11775359, compound

Product 1

HCID 21106341HCID 21106341, compoundYield 119.9%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 6-iodo-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (prepared as in Example 1, 400 mg, 1.23 mmol) in tetrahydrofuran (20 mL) at 25° C. was treated with sodium hydroxide (98 mg, 2.46 mmol), methyl iodide (0.09 mL, 1.48 mmol), and tetrabutylammonium bromide (198 mg, 0.62 mmol and stirred at 25° C. for 18 h. The resulting mixture was treated with ethyl acetate, water, and a saturated aqueous sodium chloride solution, shaken and separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 6-iodo-7-methyl-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (500 mg) as a yellow solid. The product was taken on into the next reaction without further purification.

Workup

  1. customseparated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ba7dc066f94445fa00684cfba363bed
Source dataset
uspto-grants-2007_06
Patent number
US07226915B2

Reaction notes

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