Triethylamine → HCID 67236226, compound

HRID 1023563Notes

Reaction equation

HRID 1023563 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:3].Cl[C:12]1[N:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.C(N(CC)CC)C>C(#N)C>[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([O:10][C:12]2[N:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 120593-IsopropylphenolHCID 825442-Chloro-5-nitropyrimidine

Product 1

HCID 67236226HCID 67236226, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(1-methylethyl)phenol (680 mg, 5 mmol, Aldrich) in acetonitrile (50 mL) were added 2-chloro-5-nitropyrimidine (800 mg, 5 mmol) and triethylamine (1.01 g, 10 mmol) and the resulting mixture was heated at reflux and stirred for 3 hours. The reaction mixture was concentrated under vacuum and water was added to the residue (80 mL). It was extracted with ethyl acetate (3 times 50 mL) and the combined organic layers were dried over sodium sulphate and evaporated to afford a brown oil, which was purified by silica gel chromatography (mobile phase: ethyl acetate: petroleum ether=0˜20%) to afford the title compound (900 mg).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux
  3. concentrationThe reaction mixture was concentrated under vacuum and water
  4. additionwas added to the residue (80 mL)
  5. extractionIt was extracted with ethyl acetate (3 times 50 mL)
  6. dry with materialthe combined organic layers were dried over sodium sulphate
  7. customevaporated
  8. customto afford a brown oil, which
  9. customwas purified by silica gel chromatography (mobile phase: ethyl acetate: petroleum ether=0˜20%)

Sources & evidence

ORD record
ord-8cb73c70e10d4a519d2aac5a7a5c448f
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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