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

HRID 410388Notes

Reaction equation

HRID 410388 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[Br:10][C:11]1[CH:12]=[C:13]([CH:15]=[C:16]([CH3:18])[CH:17]=1)[NH2:14].C(O)(=O)C>O1CCOCC1>[Br:10][C:11]1[CH:12]=[C:13]([NH:14][C:2]2[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=2)[CH:15]=[C:16]([CH3:18])[CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5889352-Chloro-4-methoxypyrimidineHCID 30185263-Bromo-5-methylaniline

Product 1

HCID 67250894N-(3-bromo-5-methylphenyl)-4-methoxypyrimidin-2-amineYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A 10-20 mL microwave vial was charged with 2-chloro-4-methoxypyrimidine (0.835 g, 5.78 mmol), 3-bromo-5-methylaniline (1.075 g, 5.78 mmol), acetic acid (0.347 mL, 6.06 mmol) and dioxane (11.55 mL). The system was purged and flushed with Ar(g) three times before sealing and heating to 120° C. for 3 hours. The mixture was cooled and stirred overnight. The light brown solids were collected by filtration and were dried in a vacuum oven overnight to yield N-(3-bromo-5-methylphenyl)-4-methoxypyrimidin-2-amine (1.7 g, 5.78 mmol, 100% yield) as a tan solid. MS ESI: [M+H]+ m/z 296.0.

Workup

  1. customThe system was purged
  2. customflushed with Ar(g) three times
  3. temperatureThe mixture was cooled
  4. filtrationThe light brown solids were collected by filtration
  5. customwere dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-842358daa5af4a84a723a68096a3efff
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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