Triethylamine → 4-Ethoxy-2-pyrrolidin-1-ylpyrimidine

HRID 386096Notes

Reaction equation

HRID 386096 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(CC)CC>C1COCC1>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[N:7]=1)[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 47372802-Chloro-4-ethoxypyrimidine

Product 1

HCID 595258964-Ethoxy-2-pyrrolidin-1-ylpyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-4-ethoxypyrimidine (3 g, 19 mol) in THF (410 mL) was added pyrrolidine (2.7 g, 38 mmol) and Et3N (5.8 g, 57 mmol) and the reaction mixture was heated to reflux overnight. The solvent was evaporated and the residue was partioned between water and EtOAc. The aqueous phase was extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered, and concentrated to give the title compound.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7a911ec2b8604f458f43e5d3f63a6713
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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