Dichloromethane → (Pivaloyloxy)methyl 4-((6-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylate

HRID 524687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524687
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:14]=[C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[NH:12][C:11]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH:22]2[C:27]([OH:29])=[O:28])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].[C:35]([O:41][CH2:42]Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37].C(Cl)Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:14]=[C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[NH:12][C:11]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH:22]2[C:27]([O:29][CH2:42][O:41][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:28])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 87885Chloromethyl pivalateHCID 73295969((6-(2,4-Dichlorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid

Produkt 1

HCID 90044007(Pivaloyloxy)methyl 4-((6-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-(((6-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid (0.12 g, 0.23 mmol) and TEA (0.06 g, 0.6 mmol) in DMF (6 mL) was added chloromethyl pivalate (0.12 g, 0.8 mmol). And the mixture was stirred at 60° C. for 3 hours, and cooled to 25° C. To the reaction mixture was added DCM (100 mL). The organic layer was washed with brine (80 mL×6) and dried over unhydrous Na2SO4. The crude product was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=8/1) to give the title compound as yellow oil (0.09 g, 62%). The compound was characterized by the following spectroscopic data:

Aufarbeitung

  1. temperaturecooled to 25° C
  2. washThe organic layer was washed with brine (80 mL×6)
  3. dry with materialdried over unhydrous Na2SO4
  4. customThe crude product was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=8/1)

Quellen und Nachweise

ORD-Eintrag
ord-c7c86253a6a54bf389bcf576c4f523b0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340538B2

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