Sodium hydride → N-(4-iodophenyl)-N-(2-methoxyethyl)pyrimidin-2-amine

HRID 1360044Notes

Reaction equation

HRID 1360044 reaction equation
Br[CH2:2][CH2:3][O:4][CH3:5].[H-].[Na+].[I:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1>CN(C=O)C.[Cl-].[Na+].O>[I:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH2:2][CH2:3][O:4][CH3:5])[C:16]2[N:17]=[CH:18][CH:19]=[CH:20][N:21]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 57762548N-(4-iodophenyl)pyrimidin-2-amine

Product 1

HCID 57762539N-(4-iodophenyl)-N-(2-methoxyethyl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Under an argon atmosphere, 2-bromoethylmethyl ether (0.14 ml) and sodium hydride (48 mg) were added to a solution of N-(4-iodophenyl)pyrimidin-2-amine (300 mg) in anhydrous DMF (1 ml), 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, followed by drying the organic layer 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 N-(4-iodophenyl)-N-(2-methoxyethyl)pyrimidin-2-amine (233 mg). NMR (H1, CDCl3): δ 3.32 (3H, s), 3.63 (2H, t, J=5.9 Hz), 4.14 (2H, t, J=5.9 Hz), 6.59 (1H, t, J=4.9 Hz), 7.09-7.13 (2H, m), 7.70-7.73 (2H, m), 8.32 (2H, d, J=4.9 Hz)

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialby drying the organic layer over anhydrous sodium sulfate
  3. customAfter removing anhydrous sodium sulfate
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica gel, eluent:hexane/chloroform=1/10)

Sources & evidence

ORD record
ord-2d0a123732734fd38e3e69a597ef40d5
Source dataset
uspto-grants-2011_02
Patent number
US07879837B2

Reaction notes

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