Potassium Carbonate → 5-[(4S)-4-Hydroxyisoxazolidin-2-ylcarbonyl]-6-(imidazo[1,2-a]pyridin-3-ylmethyl)-1-isobutyl-3-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 131580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131580
ClC1N=C(C)N([CH2:8][C:9]2[S:24][C:12]3[N:13]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:14](=[O:19])[N:15]([CH3:18])[C:16](=[O:17])[C:11]=3[C:10]=2[C:25]([N:27]2[CH2:31][C@H:30]([OH:32])[CH2:29][O:28]2)=[O:26])C=1Cl.[N:34]1[CH:35]=[CH:36][N:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=12.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[OH:32][C@@H:30]1[CH2:29][O:28][N:27]([C:25]([C:10]2[C:11]3[C:16](=[O:17])[N:15]([CH3:18])[C:14](=[O:19])[N:13]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:12]=3[S:24][C:9]=2[CH2:8][C:36]2[N:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]3=[N:34][CH:35]=2)=[O:26])[CH2:31]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 78960Imidazo(1,2-a)pyridineHCID 101425596-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-5-[4-(S)-hydroxy-2-isoxazolidinylcarbonyl]-3-methyl-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 102996535-[(4S)-4-Hydroxyisoxazolidin-2-ylcarbonyl]-6-(imidazo[1,2-a]pyridin-3-ylmethyl)-1-isobutyl-3-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product of example 3 part b (1 g), imidazolo[1,2-a]pyridine (0.4 ml), potassium carbonate (0.35 g) and THF (20 ml) were stirred under nitrogen for 1 h. Warer was added to the reaction and extracted with ethyl acetate (×2). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was chromatographed (SiO2/9:1 ethyl acetate-hexane and the ethyl acetate) to give the sub-title compound as a colourless oil. LCMS(ESI) 4275 [M+H]+

Aufarbeitung

  1. additionWarer was added to the reaction
  2. extractionextracted with ethyl acetate (×2)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (SiO2/9:1 ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-b1575dc6b21040b6b2bd77626b12a3cd
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384950B2

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