Sodium Iodide → 11-bromo-2,3,5,6-tetrahydro-1H-pyrrolo[2',1':3,4]pyrazino[2,1-b]quinazolin-8(13bH)-one

HRID 1619346Notes

Reaction equation

HRID 1619346 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[NH:7][C:8]([CH:12]3[CH2:16][CH2:15][CH2:14][NH:13]3)=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].Br[CH2:27][CH2:28]Cl>CC#N>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[N:7]3[CH2:28][CH2:27][N:13]4[CH2:14][CH2:15][CH2:16][CH:12]4[C:8]3=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 1360381767-bromo-2-(pyrrolidin-2-yl)quinazolin-4(3H)-one

Product 1

HCID 5857431711-bromo-2,3,5,6-tetrahydro-1H-pyrrolo[2',1':3,4]pyrazino[2,1-b]quinazolin-8(13bH)-oneYield 29.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7-bromo-2-(pyrrolidin-2-yl)quinazolin-4(3H)-one (158 mg, 0.49 mmol), K2CO3 (0.5 g, 3.6 mmol), a catalytic amount of NaI, and 1-bromo-2-chloroethane (70 mg, 0.49 mmol) in CH3CN was stirred at 80° C. overnight. After dilution with H2O (30 mL), the mixture was extracted with ethyl acetate (3×100 mL). Then the combined organic layers were dried over Na2SO4 and concentrated to give crude product. After purified by column chromatography, 46 mg of the desired product was obtained. MS (ESI): 320, 322 (MH+)

Workup

  1. extractionAfter dilution with H2O (30 mL), the mixture was extracted with ethyl acetate (3×100 mL)
  2. dry with materialThen the combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customto give crude product
  5. customAfter purified by column chromatography

Sources & evidence

ORD record
ord-309c3a10e8314b359ea1ea8dabfff243
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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