Ethylamine → 2-Chloro-N-ethyl-5-nitro-4-pyrimidinamine

HRID 1375389Notes

Reaction equation

HRID 1375389 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH2:12]([NH2:14])[CH3:13]>C1COCC1.CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:14][CH2:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 6341EthylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71472332-Chloro-N-ethyl-5-nitro-4-pyrimidinamineYield 81%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5.82 g (30 mmol) of 2,4-dichloro-5-nitropyrimidine (N. Whittaker, J. Chem. Soc., 1951:1565–1570) in 100 mL THF at −78° C. is added dropwise over 5 minutes a solution of 3.87 g (60 mmol) of 70% aqueous ethylamine in 20 mL of 2-propanol. After being stirred at −78° C. for 15 minutes, the reaction mixture is allowed to warm to room temperature, and the solvent is removed under vacuum. The residue is worked up in EtOAc and chromatographed on silica, eluting with hexane/EtOAc (92:8), to give 4.90 g (81%) of the title compound: mp (hexane) 64–66° C.

Workup

  1. temperatureto warm to room temperature
  2. customthe solvent is removed under vacuum
  3. customchromatographed on silica
  4. washeluting with hexane/EtOAc (92:8)

Sources & evidence

ORD record
ord-2456a2109e0c4bcf9dd384972c3f8298
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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