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

HRID 32303Notes

Reaction equation

HRID 32303 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[O:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[CH:6][CH:5]=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>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[O:15][CH2:14][CH2:13][N:12]([C:17]3[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)[N:18]=3)[CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 68884493(S)-2-(4-methoxyphenyl)morpholine hydrochloride

Product 1

HCID 11773349(S)-2-[2-(4-Methoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-oneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-(4-methoxyphenyl)morpholine hydrochloride (1.02 g, 4.44 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (0.76 g, 3.42 mmol) and triethylamine (1.42 ml, 10.3 mmol) in tetrahydrofuran (20 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 diethyl ether to give the title compound (1.22 g, 95%).

Workup

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

Sources & evidence

ORD record
ord-7f6f58e8369842b48c58e3fb5cb01263
Source dataset
uspto-grants-2008_09
Patent number
US07427615B2

Reaction notes

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