Ethylamine → (5-Bromo-4-methoxy-pyrimidin-2-yl)-ethyl-amine

HRID 709970Notes

Reaction equation

HRID 709970 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH2:11]([NH2:13])[CH3:12]>C1COCC1.O>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5]([NH:13][CH2:11][CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6341EthylamineHCID 36631435-Bromo-2-chloro-4-methoxypyrimidine

Product 1

HCID 59613034(5-Bromo-4-methoxy-pyrimidin-2-yl)-ethyl-amineYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-bromo-2-chloro-4-methoxypyrimidine (0.6 g, 2.69 mmol) in THF (10 mL) was treated with ethylamine (2.0M in THF, 6.71 mL, 13.43 mmol) was heated at 60° C. for 1 h, cooled to RT and diluted with water. The mixture was extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified by column chromatography (EtOAc/Hex) to afford 5-bromo-N-ethyl-4-methoxypyrimidin-2-amine as a white solid (0.54 g, 87%). MS (ESI) m/z: 232.03 (M+H+).

Workup

  1. temperaturecooled to RT
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified by column chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-b37b2fbc227440eaa89bbe1d77c68c03
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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