Triethylamine → HCID 25002828, compound

HRID 1045680Notes

Reaction equation

HRID 1045680 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:13]1[N:18]([CH3:19])[C:17](=[O:20])[CH:16]=[C:15]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[N:14]=1.C(N(CC)CC)C>>[CH3:19][N:18]1[C:17](=[O:20])[CH:16]=[C:15]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[N:14]=[C:13]1[N:9]1[CH2:10][CH2:11][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31467433-PhenylpyrrolidineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-

Product 1

HCID 25002828HCID 25002828, compoundYield 88%

Procedure

A solution of 3-phenyl-pyrrolidine (449 mg, 3.05 mmol), 2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (436 mg, 1.97 mmol) and triethylamine (412 mg, 4.07 mmol) was refluxed for one hour. After removal of the solvent, the residue was partitioned between water and ethyl acetate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate/ethanol=10/1) to afford 3-methyl-2-(3-phenyl-pyrrolidin-1-yl)-6-pyridin-4-yl-3H-pyrimidin-4-one (576 mg, 88%).

Workup

  1. customAfter removal of the solvent
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate/ethanol=10/1)

Sources & evidence

ORD record
ord-abb230ab3203442caca07d29f33a3193
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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