4-Iodophenol → 2-(4-Iodophenoxy)-4,6-dimethylpyrimidine

HRID 1360039

Reaction equation

HRID 1360039 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=1.[H-].[Na+]>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 108944-IodophenolHCID 205502-Chloro-4,6-dimethylpyrimidineHCID 24758Sodium hydride

Product 1

HCID 577624972-(4-Iodophenoxy)-4,6-dimethylpyrimidineYield 68.4%

Procedure

Under an argon atmosphere, phosphorus oxychloride (2 ml) was added to 4,6-dimethyl-2-hydroxypyrimidine (400 mg), and the resulting mixture was stirred for 1 hour while heating the mixture to reflux. The reaction solution was cooled to room temperature, and the cooled solution was added in small portions to water. After adding sodium hydrogen carbonate in small portions to the resulting mixture to neutralize it, the mixture was extracted with ethyl acetate. Organic layer was washed twice with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated to obtain 2-chloro-4,6-dimethylpyrimidine (350 mg). (2) In the same manner as in Reference Example 8, 4-iodophenol (223 mg) and 2-chloro-4,6-dimethylpyrimidine (157 mg) were reacted by using sodium hydride to obtain 2-(4-iodophenoxy)-4,6-dimethylpyrimidine (226 mg).

Sources & evidence

ORD record
ord-a1a8f4f815514301b7495aa3c141c5a6
Source dataset
uspto-grants-2011_02
Patent number
US07879837B2

Linked notes

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