Diisopropylethylamine → 5-Bromo-N-methylpyrimidin-2-amine

HRID 1042738Notes

Reaction equation

HRID 1042738 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.Cl.CN.[CH:12]([N:15](C(C)C)CC)(C)C>C(#N)C>[Br:8][C:5]1[CH:4]=[N:3][C:2]([NH:15][CH3:12])=[N:7][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 6364545Methylamine hydrochloride

Product 1

HCID 130981845-Bromo-N-methylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-5-bromopyrimidine (2.5 g, 13 mmol), methylamine hydrochloride (7.9 g, 116 mmol), and diisopropylethylamine (18 mL, 103 mmol) in 43 mL acetonitrile was heated in a sealed vessel for 16 h. The reaction was partitioned between EtOAc and water. The organic layer was washed once with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 5-bromo-N-methylpyrimidin-2-amine. MS m/z=188 [M+H]+. Calc'd for C5H6BrN3: 187.

Workup

  1. temperaturewas heated in a sealed vessel for 16 h
  2. customThe reaction was partitioned between EtOAc and water
  3. washThe organic layer was washed once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13d77d4efad04324a2527847d166f0fb
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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