Ethylamine → 6-Chloro-n4-ethylpyrimidine-2,4-diamine

HRID 2367182Notes

Reaction equation

HRID 2367182 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH2:10]([NH2:12])[CH3:11]>>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:12][CH2:10][CH3:11])[CH:7]=1

Participants

3

Reactant 2

HCID 6341EthylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 2290506-Chloro-n4-ethylpyrimidine-2,4-diamineYield 69.9%

Procedure

In a 50 mL flask under argon were combined 4,6-dichloro-2-pyrimidinamine (0.50 g, 3.05 mmol) and ethylamine (2.0 M in CH3OH) (15.24 mL, 30.5 mmol) and the reaction mixture was stirred at 50° C. for 3 hours. The mixture was cooled to room temperature and concentrated. The resulting yellow solid was dissolved in EtOAc and the solution was washed with water. The organic layer was dried (MgSO4), filtered and concentrated to afford the title compound (368 mg, 69%) as a yellow solid. LC-MS (ES) m/z=173 [M+H]+.

Workup

  1. customIn a 50 mL flask under argon were combined
  2. concentrationconcentrated
  3. dissolutionThe resulting yellow solid was dissolved in EtOAc
  4. washthe solution was washed with water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fa47a8057d0c4b629761e6cb42d3a9cf
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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