Ammonia → 6-(2-Methoxyphenyl)pyrimidin-4-amine

HRID 1020069Notes

Reaction equation

HRID 1020069 reaction equation
[NH3:1].Cl[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[N:6]=[CH:5][N:4]=1>O1CCOCC1>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[N:6]=[CH:5][N:4]=[C:3]([NH2:1])[CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 152068354-Chloro-6-(2-methoxyphenyl)pyrimidine

Product 1

HCID 497584396-(2-Methoxyphenyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

25% ammonia solution (10 ml) was added to a solution of 4-chloro-6-(2-methoxy-phenyl)-pyrimidine (2 g, 9.06 mmol) in 1,4-dioxane (10 ml) and the mixture was heated in a sealed tube at 110° C. for 8 hours with continuous stirring. The reaction mixture was allowed to cool to room temperature, concentrated under reduced pressure and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated under vacuum to give 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine as a white solid. Yield: 1.6 g, 87.9%.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-03b4d37de85640c0a034fd7f404c4385
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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