Triethylamine → 2-(2-benzoylmorpholin-4-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 32311Notes

Reaction equation

HRID 32311 reaction equation
Cl.[C:2]([CH:10]1[O:15][CH2:14][CH2:13][NH:12][CH2:11]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:17]1[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[N:18]=1.C(N(CC)CC)C>O1CCCC1>[C:2]([CH:10]1[O:15][CH2:14][CH2:13][N:12]([C:17]2[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[N:18]=2)[CH2:11]1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 688845172-Benzoylmorpholine hydrochloride

Product 1

HCID 101775342-(2-benzoylmorpholin-4-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-oneYield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-benzoylmorpholine hydrochloride (269 mg, 1.17 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (320 mg, 1.41 mmol) and triethylamine (0.49 ml, 3.51 mmol) in tetrahydrofuran (10 ml) was refluxed for several hours. The precipitate was filtered off after cooling and solvent was removed in vacuo. The residue was washed with refluxing ethyl acetate and diethyl ether to give the title compound (447 mg, quant.).

Workup

  1. filtrationThe precipitate was filtered off
  2. temperatureafter cooling
  3. customsolvent was removed in vacuo
  4. washThe residue was washed with refluxing ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-c4bbb918c04b4be79b3915bb3539d92a
Source dataset
uspto-grants-2008_09
Patent number
US07427615B2

Reaction notes

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