3-Bromopropionitrile → HCID 57762584, compound

HRID 1360047Notes

Reaction equation

HRID 1360047 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][CH2:19][C:20]#[N:21]>CN(C=O)C.[Cl-].[Na+].O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:18][CH2:19][C:20]#[N:21])[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 170203-BromopropionitrileHCID 24758Sodium hydrideHCID 57762548N-(4-iodophenyl)pyrimidin-2-amine

Product 1

HCID 57762584HCID 57762584, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

Under an argon atmosphere, a solution of N-(4-iodophenyl)pyrimidin-2-amine (100 mg) in anhydrous DMF (1.0 ml) was added to a suspension of sodium hydride (16 mg) in anhydrous DMF (1.0 ml), and the resulting mixture was stirred at room temperature for 30 minutes. To the reaction solution, a solution of 3-bromopropionitrile (0.04 ml) in anhydrous DMF (0.5 ml) was added, and the resulting mixture was stirred at room temperature overnight. Saturated brine was added to the reaction solution and the resulting mixture was extracted with chloroform. Organic layer was dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: hexane/chloroform=1/10) to obtain 3-(N-(4-iodophenyl)-N-(pyrimidin-2-yl)amino)propanenitrile (94 mg). NMR (H1, CDCl3): δ 2.82 (2H, t, J=6.8 Hz), 4.24 (2H, t, J=6.8 Hz), 6.68 (1H, t, J=4.9 Hz), 7.06-7.10 (2H, m), 7.74-7.78 (2H, m), 8.35 (2H, d, J=4.9 Hz)

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. extractionthe resulting mixture was extracted with chloroform
  3. dry with materialOrganic layer was dried over anhydrous sodium sulfate
  4. customAfter removing anhydrous sodium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by column chromatography (silica gel, eluent: hexane/chloroform=1/10)

Sources & evidence

ORD record
ord-f7b804f4e6d247448db48f7eb9bee574
Source dataset
uspto-grants-2011_02
Patent number
US07879837B2

Reaction notes

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