Water → HCID 66912002, compound

HRID 1752062Notes

Reaction equation

HRID 1752062 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.Cl[C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][N:13]=1.O>CN(C=O)C>[I:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][N:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108934-IodoanilineHCID 24758Sodium hydrideHCID 5889352-Chloro-4-methoxypyrimidine

Product 1

HCID 66912002HCID 66912002, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

Under an argon atmosphere, sodium hydride (100 mg) was added to a solution of 4-iodoaniline (220 mg) and 2-chloro-4-methoxypyrimidine (145 mg) in anhydrous DMF (10 ml), and the resulting mixture was stirred at 125° C. for 21 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extracting the resulting mixture 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. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate=10/1) to obtain N-(4-iodophenyl)-4-methoxypyrimidin-2-amine (46 mg). (2) Under an argon atmosphere, N-(4-iodophenyl)-4-methoxypyrimidin-2-amine (46 mg) was added to a suspension of sodium hydride (11 mg) in anhydrous DMF (5 ml), and the resulting mixture was stirred at room temperature for 5 minutes. Methyl iodide (0.0096 ml) was added dropwise to the reaction solution, and the resulting mixture was stirred at room temperature for 23 hours. Water was added thereto and the resulting 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. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate=3/1) to obtain N-(4-iodophenyl)-4-methoxy-N-methylpyrimidin-2-amine (46 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionby extracting the resulting mixture with ethyl acetate
  3. washOrganic layer was washed twice with water and once with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing anhydrous sodium sulfate
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-e84c437a59204f6791458118d3098c07
Source dataset
uspto-grants-2015_10
Patent number
US09162988B2

Reaction notes

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