Triethylamine → N-(4-((2S)-4-(1-Methyl-6-oxo-4-(pyridin-4-yl)-1,6-dihydropyrimidin-2-yl)morpholin-2-yl)phenyl)acetamide

HRID 424419Notes

Reaction equation

HRID 424419 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][C@@H:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=2)[CH2:2]1.Cl[C:18]1[N:19]([CH3:31])[C:20](=[O:30])[CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:23]=1.C(N(CC)CC)C>O1CCCC1>[CH3:31][N:19]1[C:20](=[O:30])[CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:23]=[C:18]1[N:1]1[CH2:6][CH2:5][O:4][C@@H:3]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:11][CH:12]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 66594379N-(4-((2S)-morpholin-2-yl)phenyl)acetamide

Product 1

HCID 66703937N-(4-((2S)-4-(1-Methyl-6-oxo-4-(pyridin-4-yl)-1,6-dihydropyrimidin-2-yl)morpholin-2-yl)phenyl)acetamideYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(4-((2S)-morpholin-2-yl)phenyl)acetamide (2.63 g, 11.9 mmol), 2-chloro-1-methyl-6-oxo-4-(pyridin-4-yl)-1,6-dihydropyrimidine (2.60 g, 11.9 mmol), and triethylamine (3.60 g, 35.7 mmol) in tetrahydrofuran (100 ml) was stirred at 95° C. for one hour. The solvent was removed in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography on silica gel (chloroform-methanol, 10:1) to afford N-(4-((2S)-4-(1-Methyl-6-oxo-4-(pyridin-4-yl)-1,6-dihydropyrimidin-2-yl)morpholin-2-yl)phenyl)acetamide (2.8 g, 58%) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-7aedd97b700241f3a9ea4f9adb695efd
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

Loading…