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Triphenylphosphine → 9-(3-cyclopropyl-propoxy)-2-((S)-1-[1,4]dioxan-2-ylmethoxy)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one

HRID 1773297
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773297
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][C@H:2]1[CH2:7][O:8][C:9]1[CH:23]=[C:13]2[C:14]3[C:19]([CH2:20][CH2:21][N:12]2[C:11](=[O:24])[N:10]=1)=[CH:18][C:17]([OH:22])=[CH:16][CH:15]=3.C[C:26]([CH3:32])([CH3:31])[CH2:27][CH2:28][CH2:29]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH:26]1([CH2:27][CH2:28][CH2:29][O:22][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[C:13]2=[CH:23][C:9]([O:8][CH2:7][C@@H:2]4[CH2:3][O:4][CH2:5][CH2:6][O:1]4)=[N:10][C:11](=[O:24])[N:12]2[CH2:21][CH2:20]3)[CH2:31][CH2:32]1
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Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 183934,4-Dimethyl-1-pentanolHCID 5363146Diisopropyl azodicarboxylateHCID 136409086(S)-2-((1,4-dioxan-2-yl)methoxy)-9-hydroxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one

Produkt 1

HCID 866884619-(3-cyclopropyl-propoxy)-2-((S)-1-[1,4]dioxan-2-ylmethoxy)-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Intermediate 6 (2.12 g, 2.42 mmol, 1 eq.), 4,4-dimethyl-pentan-1-ol (0.77 g, 7.71 mmol, 1.2 eq.) and PPh3 (2.02 g, 7.71 mmol, 1.2 eq.) were suspended in 1,4-dioxane (50 mL) and the mixture was degassed with N2. DIAD (1.56 mL, 7.71 mmol, 1.1 eq.) was added dropwise and the reaction was stirred at RT for 2 h. The reaction mixture was quenched with brine and extracted with EtOAc, the organic phase was dried over MgSO4 and evaporated to dryness. Compound 143 was obtained by purification by flash chromatography on silica gel, eluting from 60 to 100% EtOAc/H.

Aufarbeitung

  1. customthe mixture was degassed with N2
  2. customThe reaction mixture was quenched with brine
  3. extractionextracted with EtOAc
  4. dry with materialthe organic phase was dried over MgSO4
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e679162b4c9945d9aea37e0913b2ad19
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255095B2

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