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

HRID 502782Notes

Reaction equation

HRID 502782 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-abdd6fb2d9cf4f5bb0f6d5b77fbb8481
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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