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

HRID 1786868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786868
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 860847854-Iodo-6-phenoxy-5-pyrimidinamineAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-ded10e89a71c4d389ae0f9a7b910f953
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507740B2

Notizen zur Reaktion

Wird geladen…