Triethylamine → 2-[(2S)-2-(4-aminophenyl)morpholin-4-yl]-3-methyl-6-(pyridin-4-yl)-pyrimidin-4(3H)-one

HRID 424446Notes

Reaction equation

HRID 424446 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][C@@H:3]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH2:2]1.Cl[C:15]1[N:20]([CH3:21])[C:19](=[O:22])[CH:18]=[C:17]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[N:16]=1.C(N(CC)CC)C>O1CCCC1>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([C@@H:3]2[O:4][CH2:5][CH2:6][N:1]([C:15]3[N:20]([CH3:21])[C:19](=[O:22])[CH:18]=[C:17]([C:23]4[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=4)[N:16]=3)[CH2:2]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 66594670(S)-4-(Morpholin-2-yl)aniline

Product 1

HCID 667039212-[(2S)-2-(4-aminophenyl)morpholin-4-yl]-3-methyl-6-(pyridin-4-yl)-pyrimidin-4(3H)-oneYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-((2S)-morpholin-2-yl)phenylamine (0.17 g, 0.95 mmol), 2-chloro-3-methyl-4-oxo-6-(pyridin-4-yl)-3,4-dihydropyrimidine (0.17 g, 0.76 mmol), and triethylamine (0.25 g, 2.85 mmol) in tetrahydrofuran (10 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 silica gel column chromatography (chloroform/methanol=10/1) to afford 2-[(2S)-2-(4-aminophenyl)morpholin-4-yl]-3-methyl-6-(pyridin-4-yl)-pyrimidin-4(3H)-one (0.15 g, 54%) 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 silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-2062db59f4b64eb4b524647e9836ba7d
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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