Phenol → 4-Iodo-6-phenoxy-5-pyrimidinamine

HRID 1925958Notes

Reaction equation

HRID 1925958 reaction equation
[I:1][C:2]1[C:7]([NH2:8])=[C:6](I)[N:5]=[CH:4][N:3]=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[I:1][C:2]1[C:7]([NH2:8])=[C:6]([O:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 118101544,6-Diiodopyrimidin-5-amine

Product 1

HCID 860847854-Iodo-6-phenoxy-5-pyrimidinamineYield 100.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

4,6-Diiodopyrimidin-5-amine (2.2 g) was dissolved in 1-methyl-2-pyrrolidone (11.5 mL), phenol (656 mg) and potassium carbonate (964 mg) were added, and the mixture was stirred at 100° C. for 16 hrs. After cooling to room temperature, the mixture was diluted with ethyl acetate (200 mL) and washed successively with water (100 mL) and saturated brine (100 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→20:80) to give the title compound (2.0 g) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed successively with water (100 mL) and saturated brine (100 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→20:80)

Sources & evidence

ORD record
ord-7b6611cb0c534133b0051b496a0e4bf9
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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