Diisopropylethylamine → N-[2-(3-Bromo-4-methoxyphenyl)ethyl]-5-ethylpyrimidin-2-amine

HRID 2251494Notes

Reaction equation

HRID 2251494 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH2:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl[C:14]1[N:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][N:15]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH:12][C:14]2[N:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27355812-(3-Bromo-4-methoxyphenyl)ethan-1-amineHCID 35727632-Chloro-5-ethylpyrimidine

Product 1

HCID 59643362N-[2-(3-Bromo-4-methoxyphenyl)ethyl]-5-ethylpyrimidin-2-amineYield 67.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-(3-bromo-4-methoxyphenyl)ethanamine (1 g; 4.35 mmol), 2-chloro-5-ethyl-pyrimidine (0.56 g; 3.92 mmol) and DIEA (0.84 g; 6.53 mmol) in n-butanol was heated to reflux for 14 hr. Upon cooling, the reaction mixture was concentrated and partitioned between 1N HCl and ether. The aqueous phase was basified with 6N NaOH and extracted with ether. The combined organic phases were washed with a saturated solution of NaHCO3, dried over MgSO4, filtered and concentrated to provide a colorless solid, which was triturated with hexane, filtered and dried to provide the title compound as a white crystalline solid (0.89 g; 67% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 14 hr
  3. temperatureUpon cooling
  4. concentrationthe reaction mixture was concentrated
  5. custompartitioned between 1N HCl and ether
  6. extractionextracted with ether
  7. washThe combined organic phases were washed with a saturated solution of NaHCO3
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto provide a colorless solid, which
  12. customwas triturated with hexane
  13. filtrationfiltered
  14. customdried

Sources & evidence

ORD record
ord-efa2243913b94902911c4a5d17fe3428
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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