Cyclopropylamine → 5-bromo-N-cyclopropylpyrimidin-2-amine

HRID 706807Notes

Reaction equation

HRID 706807 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH:9]1([NH2:12])[CH2:11][CH2:10]1>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:12][CH:9]2[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 50233275-bromo-N-cyclopropylpyrimidin-2-amineYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-2-chloropyrimidine (3.87 g, 20 mmol) and cyclopropylamine (5.7 g, 0.1 mol) in 20 mL THF was heated at 65° C. for 5 hrs in a sealed tube. The mixture was evaporated in vacuo, to the residue ethanol was added, after filtration, the cake was washed with ethanol to give 4.07 g product as a colorless solid (95.5%). 1H NMR (300 MHz, CDCl3) δ: 8.32 (2 H, s), 5.58 (1 H, brs), 2.72 (1 H, brs), 0.82-0.84 (2 H, m), 0.54 (2 H, brs). LCMS: m/z [M+H]+ 214.0011.

Workup

  1. customThe mixture was evaporated in vacuo, to the residue ethanol
  2. additionwas added
  3. filtrationafter filtration
  4. washthe cake was washed with ethanol

Sources & evidence

ORD record
ord-45b77efa882b46dab7e4afe58bcfcf3a
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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