Sodium hydride → 4-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]-benzaldehyde

HRID 584362Notes

Reaction equation

HRID 584362 reaction equation
[H-].[Na+].[CH3:3][N:4]([C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:5][CH2:6][OH:7].F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH3:3][N:4]([C:8]1[N:9]=[CH:10][CH:11]=[CH:12][N:13]=1)[CH2:5][CH2:6][O:7][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 10419381Ethanol, 2-(methyl-2-pyrimidinylamino)-HCID 21226206Ethyl acetate hexane

Product 1

HCID 100380894-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]-benzaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% in oil, 4.40 g) was added to a solution of 2-(methyl-2-pyrimidylamino)ethanol (15.3 g) in N,N-dimethylformamide (400 ml) at room temperature under nitrogen atmosphere and stirred for 1 hour. A solution of 4-fluorobenzaldehyde (13.6 g) in N,N-dimethylformamide (100 ml) was added dropwise and stirred at room temperature for 15 hours. The reaction mixture was poured onto ice (200 g) and concentrated. The residue was dissolved in ethyl acetate, washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain 4-[2-(methyl-2-pyrimidylamino)ethoxy]benzaldehyde (18.4 g, yield 72%) as crystals from an ethyl acetate-hexane (1:1, v/v)-eluted fraction. Recrystallization from ethyl acetate-hexane gave colorless crystals. m.p. 74-75° C.

Workup

  1. stirringstirred at room temperature for 15 hours
  2. additionThe reaction mixture was poured onto ice (200 g)
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with an aqueous saturated solution of sodium chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b727aaa82b1c43adb268904e82ebc049
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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