Acetic Acid → N-(3-bromo-5-methylphenyl)-4-methylpyrimidin-2-amine

HRID 1039876

Reaction equation

HRID 1039876 reaction equation
C(O)(=O)C.Cl[C:6]1[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][N:7]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[NH2:17]>O1CCOCC1>[Br:13][C:14]1[CH:15]=[C:16]([NH:17][C:6]2[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][N:7]=2)[CH:18]=[C:19]([CH3:21])[CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 30185263-Bromo-5-methylanilineHCID 116296072-Chloro-4-methylpyrimidine

Product 1

HCID 67249356N-(3-bromo-5-methylphenyl)-4-methylpyrimidin-2-amineYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Acetic acid (0.234 mL, 4.08 mmol) was added to 2-chloro-4-methylpyrimidine (0.5 g, 3.89 mmol) and 3-bromo-5-methylaniline (1.096 g, 3.89 mmol) suspended in dioxane (7.78 mL). The reaction was heated to 120° C. overnight. Then, the reaction was cooled to room temperature and was directly purified by column chromatography on silica gel eluting with ethyl acetate/hexanes to give N-(3-bromo-5-methylphenyl)-4-methylpyrimidin-2-amine (1.08 g, 3.89 mmol, quant.) as a white solid. MS ESI: [M+H]+ m/z 278.0 and 280.0.

Workup

  1. temperatureThen, the reaction was cooled to room temperature
  2. customwas directly purified by column chromatography on silica gel eluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-70deb626fe5c4457b6daf6a44871850d
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Linked notes

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