Water → ethyl 2-[N-ethyl-N-(3,5-di-tert-butylphenyl)amino]pyrimidine-5-carboxylate

HRID 984877Notes

Reaction equation

HRID 984877 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:15][C:16]2[N:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=2)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:29](I)[CH3:30].O>CN(C=O)C>[CH2:29]([N:15]([C:16]1[N:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=1)[C:7]1[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1)[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22509303HCID 22509303, compound

Product 1

HCID 22509301ethyl 2-[N-ethyl-N-(3,5-di-tert-butylphenyl)amino]pyrimidine-5-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethyl 2-[N-(3,5-di-tert-butylphenyl)amino]pyrimidine-5-carboxylate (50 mg) was dissolved in dry DMF (2 ml), and the solution was added with a suspension of NaH (45 mg) in DMF (1 ml). The mixture was then added with ethyl iodide (0.3 ml) and stirred. After the disappearance of the materials was observed with TLC, the reaction mixture was poured into water, and extracted with CH2Cl2. The organic layer was dried over Na2SO4, and the solvent was evaporated. The residue was purified by silica gel flash column chromatography (n-hexane: AcOEt=10:1) to obtain white crystals of ethyl 2-[N-ethyl-N-(3,5-di-tert-butylphenyl)amino]pyrimidine-5-carboxylate (53 mg, 99%).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel flash column chromatography (n-hexane: AcOEt=10:1)

Sources & evidence

ORD record
ord-68b2f77c53e9480dba8c68a790c641a7
Source dataset
uspto-grants-2005_03
Patent number
US06869959B1

Reaction notes

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