Sodium hydride → (4-Acetoxybenzyl)-(4-iodophenyl)pyrimidin-2-ylamine

HRID 230306Notes

Reaction equation

HRID 230306 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+].[C:17]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1)(=[O:19])[CH3:18]>CN(C=O)C.[Cl-].[Na+].O>[C:17]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:23][CH:22]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1483124-(Chloromethyl)phenyl acetateHCID 57762548N-(4-iodophenyl)pyrimidin-2-amine

Product 1

HCID 57762581(4-Acetoxybenzyl)-(4-iodophenyl)pyrimidin-2-ylamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

Under an argon atmosphere, a solution of N-(4-iodophenyl)pyrimidin-2-amine (68 mg) in anhydrous DMF (1.0 ml) was added dropwise to a solution 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 4-acetoxybenzyl chloride (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/ethyl acetate=6/1) to obtain (4-acetoxybenzyl)-(4-iodophenyl)pyrimidin-2-ylamine (67 mg). NMR (HL, CDCl3): δ 2.28(3H, s), 5.22 (2H, s), 6.63 (1H, t, J=4.6 Hz), 6.98-7.02 (4H, m), 7.26 (2H, d, J=8.1 Hz), 7.64-7.67 (2H, m), 8.34 (2H, d, J=4.6 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/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-ea015798cbd74408b4a8c69acb5788bf
Source dataset
uspto-grants-2009_07
Patent number
US07566724B2

Reaction notes

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