Triethylamine → 4-Ethylamino-5-nitro-2-phenylpyrimidine

HRID 842062Notes

Reaction equation

HRID 842062 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.Cl.[CH2:18]([NH2:20])[CH3:19].C(N(CC)CC)C>C(O)(C)C>[CH2:18]([NH:20][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1)[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 22617793HCID 22617793, compound

Product 1

HCID 226177974-Ethylamino-5-nitro-2-phenylpyrimidineYield 93.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-5-nitro-2-phenylpyrimidine (3 g), ethylamine hydrochloride (1.6 g), triethylamine (3.9 g) and isopropanol (60 ml) is refluxed for three hours. The reaction mixture is concentrated under reduced pressure, and to the residue are added chloroform and water. The chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from isopropanol to give the desired compound (2.9 g).

Workup

  1. temperatureis refluxed for three hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionto the residue are added chloroform and water
  4. customThe chloroform layer is separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-857f86fbe7524e19a8d3afb9365d8686
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

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