Acetic Acid → HCID 67431932, compound

HRID 410402Notes

Reaction equation

HRID 410402 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Br:9])[CH:8]=1)[NH2:5].Cl[C:11]1[N:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=1.C(O)(=O)C>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:11]2[N:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=2)[CH:6]=[C:7]([Br:9])[CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2215123,5-DibromoanilineHCID 116296072-Chloro-4-methylpyrimidine

Product 1

HCID 67431932HCID 67431932, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 3,5-dibromoaniline (2.93 g, 11.67 mmol), 2-chloro-4-methylpyrimidine (1.5 g, 11.67 mmol), and acetic acid (0.701 mL, 12.25 mmol) in 1,4-dioxane (23.5 mL) was sealed in a pressure vessel under an argon atmosphere and heated at 120° C. for 17 hours. After being cooled to room temperature, the reaction mixture was partitioned between ethyl acetate (100 mL) and saturated aqueous sodium bicarbonate solution (40 mL). The layers were separated, and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. Silica gel flash chromatography (10% to 30% ethyl acetate/hexanes) afforded N-(3,5-dibromophenyl)-4-methylpyrimidin-2-amine (3.6 g, 9.97 mmol, 85% yield, 95% purity) as a light yellow solid. MS ESI: [M+H]+ m/z 343.8.

Workup

  1. temperatureAfter being cooled to room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate (100 mL) and saturated aqueous sodium bicarbonate solution (40 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1b975ec9708e468f9322f87067e51f57
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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