Trifluoroacetic acid → 10-(5-Chlorofuran-2-yl)-8-((1,3-dioxoisoindolin-2-yl)methyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione

HRID 624581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624581
FC(F)(F)C(O)=O.C([Si](C)(C)[O:13][CH:14]([CH2:35][N:36]1[C:44](=[O:45])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]1=[O:46])[CH2:15][N:16]1[C:24]([C:25]2[S:26][CH:27]=[C:28]([CH3:30])[N:29]=2)=[C:23]2[C:18]([N:19]([CH3:34])[C:20](=[O:33])[N:21]([CH3:32])[C:22]2=[O:31])=[CH:17]1)(C)(C)C.[O-]S(C(F)(F)F)(=O)=O.[Bi+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[Cl:74][C:75]1[O:79][C:78]([CH:80]=O)=[CH:77][CH:76]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:74][C:75]1[O:79][C:78]([CH:80]2[C:17]3=[C:18]4[N:19]([CH3:34])[C:20](=[O:33])[N:21]([CH3:32])[C:22](=[O:31])[C:23]4=[C:24]([C:25]4[S:26][CH:27]=[C:28]([CH3:30])[N:29]=4)[N:16]3[CH2:15][CH:14]([CH2:35][N:36]3[C:37](=[O:46])[C:38]4[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:44]3=[O:45])[O:13]2)=[CH:77][CH:76]=1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 27696305-Chloro-2-furaldehydeHCID 9917655Bi(OTf)3HCID 867229056-(2-((tert-Butyldimethylsilyl)oxy)-3-(1,3-dioxoisoindolin-2-yl)propyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Produkt 1

HCID 8672290710-(5-Chlorofuran-2-yl)-8-((1,3-dioxoisoindolin-2-yl)methyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (0.032 ml, 0.421 mmol) was added to a solution of 6-(2-((tert-butyldimethyl silyl)oxy)-3-(1,3-dioxoisoindolin-2-yl)propyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (50 mg, 0.084 mmol) in toluene (1 ml) and the mixture was stirred for 30 mins. Bismuth triflate (27.6 mg, 0.042 mmol) and 5-chlorofuran-2-carbaldehyde (16.49 mg, 0.126 mmol) were added and the mixture stirred at room temperature for 16 hours. The mixture was diluted with ethyl acetate (30 ml) and washed with water (30 ml), saturated NaHCO3(aq) (50 ml) and brine (50 ml). The organic layer was dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-100% EtOAc/hexane, afforded the title compound.

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for 16 hours
  2. washwashed with water (30 ml), saturated NaHCO3(aq) (50 ml) and brine (50 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 0-100% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e9230d5fa004491f97c6ad248fd3c140
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303035B2

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