Triethylamine → 3-Methyl-2-((2S)-2-(4-(methyl(pyridin-2-yl)amino)phenyl)morpholin-4-yl)-6-(pyridin-4-yl)-pyrimidin-4(3H)-one

HRID 424429Notes

Reaction equation

HRID 424429 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[O:20][CH2:19][CH2:18][NH:17][CH2:16]2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.Cl[C:22]1[N:23]([CH3:35])[C:24](=[O:34])[CH:25]=[C:26]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[N:27]=1.C(N(CC)CC)C>O1CCCC1>[CH3:35][N:23]1[C:24](=[O:34])[CH:25]=[C:26]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[N:27]=[C:22]1[N:17]1[CH2:18][CH2:19][O:20][C@@H:15]([C:12]2[CH:11]=[CH:10][C:9]([N:2]([CH3:1])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=3)=[CH:14][CH:13]=2)[CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 66703969N-Methyl-N-(4-((2S)-morpholin-2-yl)phenyl)pyridin-2-amine

Product 1

HCID 667040843-Methyl-2-((2S)-2-(4-(methyl(pyridin-2-yl)amino)phenyl)morpholin-4-yl)-6-(pyridin-4-yl)-pyrimidin-4(3H)-oneYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-Methyl-N-(4-((2S)-morpholin-2-yl)phenyl)pyridin-2-amine (0.12 g, 0.46 mmol), 2-chloro-1-methyl-6-oxo-4-(pyridin-4-yl)-1,6-dihydropyrimidine (0.08 g, 0.37 mmol), and triethylamine (0.23 g, 2.3 mmol) in tetrahydrofuran (10 ml) was stirred at 95° C. for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (chloroform-methanol, 10:1) to give 3-Methyl-2-((2S)-2-(4-(methyl(pyridin-2-yl)amino)phenyl)morpholin-4-yl)-6-(pyridin-4-yl)-pyrimidin-4(3H)-one (65 mg, 13%) as a yellow oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel (chloroform-methanol, 10:1)

Sources & evidence

ORD record
ord-e1dbafdb034c4c1a92632b509ad0ab15
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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