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Dimethylacetamide → 6-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile

HRID 522257
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 522257
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C[C:23]([N:25](C)C)=O.Cl[C:29]1[N:37]=[C:36]2[C:32]([N:33]=[CH:34][N:35]2[CH3:38])=[C:31]([C:39]2[CH:44]=[CH:43][C:42]([O:45]CC3C=CC(OC)=CC=3)=[C:41]([C:55]([F:58])([F:57])[F:56])[CH:40]=2)[N:30]=1>[Zn].[C-]#N.[Zn+2].[C-]#N.FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O.O>[OH:45][C:42]1[CH:43]=[CH:44][C:39]([C:31]2[N:30]=[C:29]([C:23]#[N:25])[N:37]=[C:36]3[C:32]=2[N:33]=[CH:34][N:35]3[CH3:38])=[CH:40][C:41]=1[C:55]([F:56])([F:57])[F:58]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 31374DimethylacetamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 1178996942-chloro-6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine

Produkt 1

HCID 1370152256-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11186
Zinc cyanide (Zn(CN)2)
Katalysator
HCID 23994ZincKatalysator
HCID 2733347Palladium(II) trifluoroacetateKatalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Zinc (64 mg), 2-(di-tert-butylphosphino)biphenyl (163 mg), zinc cyanide (230 mg), and palladium (II) trifluoroacetate (81 mg) were added to a DMAc (16.5 mL) solution of 2-chloro-6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine (1.1 g) at room temperature in an argon atmosphere, and the mixture was stirred at 100° C. for 3 hours. After the reaction mixture was cooled to room temperature, water was added thereto, then extraction thereof was performed using EtOAc, and the extract was washed with water. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=1:1 to 1:4), whereby a mixture of 6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine-2-carbonitrile and 6-[4-hydroxy-3-(trifluoromethyl)phenyl]-9-methyl-9H-purine-2-carbonitrile (502 mg) was obtained.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionextraction
  3. washthe extract was washed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=1:1 to 1:4), whereby
  8. additiona mixture of 6-{4-[(4-methoxybenzyl)oxy]-3-(trifluoromethyl)phenyl}-9-methyl-9H-purine-2-carbonitrile

Quellen und Nachweise

ORD-Eintrag
ord-9ae48241993d4c53bf1f34d515d62172
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09328118B2

Notizen zur Reaktion

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