3,4-Dichlorobenzaldehyde → 3-Phenylpropyl 4-(3,4-dichlorophenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-2-(4-pyridyl)-1,4-dihydropyrimidine-5-carboxylate

HRID 324778

Reaktionsgleichung

Reaktionsgleichung von HRID 324778
[N:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH:30]=O.Cl.[C:37]([C:40]1[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=1)(=[NH:39])[NH2:38].C([O-])(=O)C.[Na+]>CN(C)C=O>[Cl:26][C:27]1[CH:28]=[C:29]([CH:30]2[C:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:14])=[C:11]([CH2:10][O:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[NH:39][C:37]([C:40]3[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=3)=[N:38]2)[CH:32]=[CH:33][C:34]=1[Cl:35]

Komponenten

6

Edukt 4

HCID 227103,4-DichlorobenzaldehydeHCID 517045Sodium AcetateHCID 2776844Pyridine-4-amidine hydrochlorideHCID 220055123-Phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate

Produkt 1

HCID 220055313-Phenylpropyl 4-(3,4-dichlorophenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-2-(4-pyridyl)-1,4-dihydropyrimidine-5-carboxylateAusbeute 3,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 3-phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate (1.50 g, 4.32 mmol), 3,4-dichlorobenzaldehyde (0.907 g, 5.18 mmol), 4-amidinopyridine hydrochloride (0.816 g, 5.18 mmol) and sodium acetate (0.425 g, 5.18 mmol) was stirred in N,N-dimethylformamide (10 mL) for 14 days at room temperature and then heated to 60° C. for 6 days. The DMF was removed in vacuo and ethyl acetate was added to the residue. The precipitate was removed by filtration and the filtrate was washed with water, sodium hydrogen carbonate solution and brine, dried and evaporated to yield an oil. The oil was further purified by flash chromatography to give the title compound (81.7 mg) as an oil.

Aufarbeitung

  1. customThe DMF was removed in vacuo and ethyl acetate
  2. additionwas added to the residue
  3. customThe precipitate was removed by filtration
  4. washthe filtrate was washed with water, sodium hydrogen carbonate solution and brine
  5. customdried
  6. customevaporated
  7. customto yield an oil
  8. customThe oil was further purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-76d939b350284a8cb06b7161a68ee743
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218538B1

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