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Butyl vinyl ether → 1-(6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-12-yl)-ethanone

HRID 513796
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 513796
[CH:1]([O:3]CCCC)=[CH2:2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].Br[C:44]1[CH:45]=[C:46]2[C:55](=[C:56]3[C:61]=1[CH:60]=[CH:59][CH:58]=[N:57]3)[NH:54][S:53](=[O:63])(=[O:62])[C:52]1[C:47]2=[CH:48][CH:49]=[CH:50][CH:51]=1>C1COCC1.Cl.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C.O>[O:62]=[S:53]1(=[O:63])[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]2[C:55](=[C:56]3[C:61](=[C:44]([C:1](=[O:3])[CH3:2])[CH:45]=2)[CH:60]=[CH:59][CH:58]=[N:57]3)[NH:54]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 1675994412-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Produkt 1

HCID 681830641-(6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-12-yl)-ethanoneAusbeute 30,5 %

Reagenzien, Katalysatoren, Lösungsmittel

5
HCID 167845palladium(II) acetateKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of DMF/H2O (4:1) was de-gassed for 15 min. DMF/H2O (4:1, 6 ml) and 1-vinyloxy-butane (0.59 ml, 4.53 mmol) were added to a mixture of Pd(OAc)2 (6 mg, 26 μmol), 1,3-bis(diphenylphosphino)propane (24 mg, 57 K2CO3 (150 mg, 1.01 mmol), 12-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 545 (370 mg, 0.91 mmol), under nitrogen. The mixture was heated at 90° C. for 2.5 h in the microwave. After cooling, the reaction was diluted with THF (2 ml) and 1M HCl (2 ml) and the mixture was stirred for 18 h. The mixture was further diluted with EtOAc (10 ml) and washed with water (10 ml, ×3). The precipitate formed during work-up was collected by filtration of the organic and aqueous phases and was found to be the title compound (140 mg, 40%). The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was triturated from MeOH to give the title compound (90 mg, 24%) which was used in the next step without further purification.

Aufarbeitung

  1. customA solution of DMF/H2O (4:1) was de-gassed for 15 min
  2. temperatureAfter cooling
  3. washwashed with water (10 ml, ×3)
  4. customThe precipitate formed during work-up
  5. filtrationwas collected by filtration of the organic and aqueous phases
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-9cf66d933baa40a1ba1220de3821cd77
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09102688B2

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